@article{Oger2025d,

title = {Synthesis of Nitrogen Heterocycles by Intramolecular Radical Addition to Alkynes: A Systematic Study},

author = {Samuel Oger and Gwilherm Evano},

doi = {10.1055/a-2661-3996},

issn = {1437-2096},

year  = {2025},

date = {2025-07-20},

urldate = {2025-07-20},

journal = {Synlett},

publisher = {Georg Thieme Verlag KG},

abstract = {<jats:title>Abstract</jats:title><jats:p>We report in this letter a systematic study of the synthesis of saturated nitrogen heterocycles by intramolecular radical addition to alkynes. In this perspective, a series of sulfonamides containing both an alkyne and an iodoalkyl subunit was synthesized and subjected to a copper-based photoredox catalyst, [Cu(bcp)DPEphos)]PF6, in the presence of Hunig’s base and under blue light irradiation. In all cases, and regardless of the position of the nitrogen atom with respect to both the alkyne and the iodide, an exclusive exo-dig cyclization was observed, with no traces of competing endo-dig products detectable. This radical cyclization enables the synthesis of azetidines, pyrrolidines, piperidines, and azepanes and, all together, these results provide a useful systematic study of radical digonal cyclizations to nitrogen heterocycles.</jats:p>},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Annibaletto2024e,

title = {Mechanistic Studies on the Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides to Indenes},

author = {Julien Annibaletto and Clément Jacob and Pierre Thilmany and Anaïs Loison and Jorge Escorihuela and Gwilherm Evano},

doi = {10.1021/acsomega.4c09973},

issn = {2470-1343},

year  = {2024},

date = {2024-12-31},

urldate = {2024-12-31},

journal = {ACS Omega},

volume = {9},

number = {52},

pages = {51690--51700},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Fang2023g,

title = {Ring-closing enyne metathesis of allylic and propargylic cyanamides},

author = {Jiaqi Fang and Sébastien Van Laethem and Nicolas Blanchard and Gwilherm Evano},

editor = {Jacques Royer},

doi = {10.24820/ark.5550190.p012.098},

issn = {1551-7012},

year  = {2024},

date = {2024-12-31},

volume = {2024},

number = {2},

publisher = {ARKAT USA, Inc.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Gérard2024d,

title = {Copper-catalyzed direct α-peroxidation of nitrogen heterocycles},

author = {Phidéline Gérard and Céline Guissart and Gwilherm Evano},

editor = {Alan Cutler},

doi = {10.24820/ark.5550190.p012.154},

issn = {1551-7012},

year  = {2024},

date = {2024-12-22},

volume = {2024},

number = {5},

publisher = {ARKAT USA, Inc.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Jacob2024d,

title = {Rhodium‐Catalyzed Direct \textit{ortho}‐Arylation of Anilines},

author = {Clément Jacob and Julien Annibaletto and Ju Peng and Ruopeng Bai and Bert U. W. Maes and Yu Lan and Gwilherm Evano},

doi = {10.1002/anie.202403553},

issn = {1521-3773},

year  = {2024},

date = {2024-07-22},

journal = {Angew Chem Int Ed},

volume = {63},

number = {30},

publisher = {Wiley},

abstract = {AbstractAn efficient and broadly applicable rhodium‐catalyzed direct ortho‐arylation of anilines with aryl iodides relying on readily available aminophosphines as traceless directing groups is reported. Its scope and functional group compatibility were both found to be quite broad as a large variety of both aminophosphines and (hetero)aryl iodides, including complex ones, could be utilized. The ortho‐arylated anilines could be obtained in high average yields, without any competing diarylation and with full regioselectivity, which constitutes a major step forward compared to other processes. The reaction is moreover not limited to aryl iodides, as an aryl bromide and a triflate could be successfully used, and could be extended to diarylation. Mechanistic studies revealed the key and unique role of the aminophosphine, acting not only as a substrate but also as a ligand for the rhodium catalyst.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Boquet2024c,

title = {Copper-Catalyzed Coupling between \textit{ortho}-Haloanilines and Lactams/Amides: Synthesis of Benzimidazoles and Telmisartan},

author = {Vincent Boquet and Chris Sauber and Raphaël Beltran and Vincent Ferey and Fabien Rodier and Pierre Hansjacob and Cédric Theunissen and Gwilherm Evano},

doi = {10.1021/acs.joc.3c02905},

issn = {1520-6904},

year  = {2024},

date = {2024-04-19},

journal = {J. Org. Chem.},

volume = {89},

number = {8},

pages = {5469--5479},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2023c,

title = {Copper-(Photo)Catalyzed Radical Reactions with Organic Halides},

author = {Gwilherm Evano and Cédric Theunissen},

doi = {10.1055/a-2095-5242},

issn = {1437-2096},

year  = {2024},

date = {2024-03-00},

journal = {Synlett},

volume = {35},

number = {05},

pages = {485--499},

publisher = {Georg Thieme Verlag KG},

abstract = {AbstractCopper is one of the most efficient and attractive metals for catalysis. In addition to their availability, low cost and limited toxicity, copper complexes are utilized to catalyze a broad variety of reactions, including examples involving radicals. For such reactions, organic halides are by far the most versatile and attractive substrates. Our contributions to the catalysis of radical reactions from organic halides with copper complexes are summarized in this account.1 	Introduction2 	Copper-Catalyzed Radical Cross-Coupling Reactions3 	Copper-Catalyzed Radical Reactions4 	Copper-Catalyzed Radical Carbonylative Cross-Coupling Reactions5 	Photoinduced, Copper-Catalyzed Radical Reactions6 	Conclusions and Outlook},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2023j,

title = {Copper-Catalyzed Carbonylative Cross-Coupling of Alkyl Iodides with Alcohols and Sodium Hydroxide: Synthesis of Esters and Carboxylic Acids},

author = {Gwilherm Evano and Omaïma Adaoudi and Julie Le Bescont and Antoine Bruneau-Voisine},

doi = {10.1055/a-2042-3417},

issn = {1437-210X},

year  = {2024},

date = {2024-02-00},

journal = {Synthesis},

volume = {56},

number = {04},

pages = {668--676},

publisher = {Georg Thieme Verlag KG},

abstract = {AbstractA general and inexpensive catalytic system is reported for the copper-catalyzed carbonylative coupling between alkyl iodides and alcohols or sodium hydroxide. Upon reaction with catalytic amounts of copper(I) chloride and N,N,N′,N′′,N′′-pentamethyldiethylenetriamine under a mild pressure of carbon monoxide (5 bar), a range of secondary and tertiary alkyl iodides are readily converted into the corresponding esters and carboxylic acids without competing direct nucleophilic substitution. Main advantages of this procedure include its broad applicability, the use of an especially inexpensive and available catalytic system, and its user-friendliness.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Grosso2023d,

title = {Copper‐Catalyzed Cross‐Coupling of Acylzirconocenes and Diaryliodonium Salts: An Efficient Synthesis of Alkyl‐aryl‐ketones from Alkenes},

author = {Simone Grosso and Marcelina Mlynczak and Gwilherm Evano and Olivier Riant},

doi = {10.1002/ejoc.202300938},

issn = {1099-0690},

year  = {2023},

date = {2023-12-13},

journal = {Eur J Org Chem},

volume = {26},

number = {47},

publisher = {Wiley},

abstract = {AbstractAn efficient and unprecedented cross‐coupling between acylzirconocenes, readily available starting materials conveniently prepared by hydrozirconation of alkenes and a subsequent carbonylation with carbon monoxide, and diaryliodonium tetrafluoroborates is reported. This procedure enables the synthesis of a broad variety of alkyl‐aryl‐ketones upon simple catalysis with copper cyanide without the need of additional ligands and only requires a low pressure of carbon monoxide generated in situ, in a two‐chamber reactor, from N‐formylsaccharin.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Fang2023h,

title = {Copper-Catalyzed, Ligand-Controlled N(sp^{3})- or N(sp)-Selective Arylation of Cyanamides},

author = {Jiaqi Fang and Oumaïma Bekkouch and Guilhem Zeiser and Yurii Zubchuk and Vincent Bizet and Nicolas Blanchard and Gwilherm Evano},

doi = {10.1021/acs.orglett.3c02622},

issn = {1523-7052},

year  = {2023},

date = {2023-09-01},

journal = {Org. Lett.},

volume = {25},

number = {34},

pages = {6446--6451},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Beaudelot2023d,

title = {Structure‐Property Relationships in a New Family of Photoactive Diimine‐Diphosphine Copper(I) Complexes},

author = {Jérôme Beaudelot and Gwilherm Evano and Cécile Moucheron},

doi = {10.1002/chem.202300758},

issn = {1521-3765},

year  = {2023},

date = {2023-07-14},

journal = {Chemistry A European J},

volume = {29},

number = {40},

publisher = {Wiley},

abstract = {AbstractA new family of heteroleptic diimine‐diphosphine copper(I) complexes is reported, with six new complexes compared to benchmark [Cu(bcp)(DPEPhos)]PF6. These new complexes are based on 1,4,5,8‐tetraazaphenanthrene (TAP) ligands with representative electronic properties as well as substitution patterns and DPEPhos and XantPhos as diphosphine ligands. Their photophysical and electrochemical properties were investigated and correlated with the number and position of substituents on the TAP ligands. Stern‐Volmer studies using Hünig's base as reductive quencher demonstrated the influence of the complex photoreduction potential and of the excited state lifetime on the photoreactivity. This study refines the structure‐property relationship profile for heteroleptic copper(I) complexes and confirms that such profiles are of high interest to design new copper complexes as optimized photoredox catalysts.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Landrain2023d,

title = {Synthesis of Tetrahydrofurans and Pyrrolidines by Copper-Catalyzed Oxy/Aminoarylation of Alkenes},

author = {Yohann Landrain and Gwilherm Evano},

doi = {10.1021/acs.orglett.3c01265},

issn = {1523-7052},

year  = {2023},

date = {2023-06-02},

journal = {Org. Lett.},

volume = {25},

number = {21},

pages = {3898--3903},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Jacob2023d,

title = {Direct Arylation of C(sp2)–H Bonds in Anilines},

author = {Clément Jacob and Gwilherm Evano and Julien Annibaletto and Bert U. W. Maes},

doi = {10.1055/a-2039-7985},

issn = {1437-210X},

year  = {2023},

date = {2023-06-00},

journal = {Synthesis},

volume = {55},

number = {12},

pages = {1799--1823},

publisher = {Georg Thieme Verlag KG},

abstract = {AbstractAnilines selectively arylated at their ortho, meta or para positions are useful building blocks in synthesis and have found applications in many areas. The most straightforward method for their synthesis relies on the direct arylation of a C(sp2)–H bond of anilines, an attractive strategy avoiding the prefunctionalization of the starting anilines provided that such arylations proceed with high levels of regioselectivity. Such reactions are presented and discussed, in a comprehensive manner, in this review article, with an emphasis on the regioselectivity of the processes and factors governing both the reactivity and selectivity. 1 	Introduction2 	ortho-Arylation of Anilines2.1 	Direct C(sp2)–H ortho-Arylation of Anilines2.2 	Directed C(sp2)–H ortho-Arylation of Anilines3 	meta-Arylation of Anilines4 	para-Arylation of Anilines4.1 	Direct C(sp2)–H para-Arylation of Anilines via Oxidative Radical Homodimerization4.2 	Direct C(sp2)–H para-Arylation of Anilines via Transition-Metal Catalysis5 	Conclusion and Outlook},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2022d,

title = {Radical Cyclization of Ynamides to Nitrogen Heterocycles},

author = {Gwilherm Evano and Chunyang Zhang and Nicolas Blanchard},

doi = {10.1055/a-1868-8092},

issn = {1437-210X},

year  = {2023},

date = {2023-01-00},

journal = {Synthesis},

volume = {55},

number = {02},

pages = {272--288},

publisher = {Georg Thieme Verlag KG},

abstract = {AbstractAn efficient radical cyclization of suitably functionalized ynamides to nitrogen-containing heterocycles is reported. Upon reaction with tributyltin hydride in the presence of catalytic amounts of AIBN in toluene at 80 °C, a range of ynamides bearing a N-iodopropyl chain could be smoothly cyclized, in a highly regio- and stereoselective manner, to the corresponding 2-arylidenepyrrolidines in good to excellent yields. The exocyclic double bond was in addition shown to be an excellent anchor for further chemical diversification and the generality of this radical cyclization could be highlighted by its extension to the synthesis of other nitrogen heterocycles including piperidines, azepanes, pyrazolidines and hexahydropyridazines.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Jos2022d,

title = {Phosphine-catalyzed regio- and stereo-selective hydroboration of ynamides to (\textit{Z})-β-borylenamides},

author = {Swetha Jos and Christine Tan and Pierre Thilmany and Alaâ Saadane and Carla Slebodnick and Gwilherm Evano and Webster L. Santos},

doi = {10.1039/d2cc04543e},

issn = {1364-548X},

year  = {2022},

date = {2022-12-13},

journal = {Chem. Commun.},

volume = {58},

number = {99},

pages = {13751--13754},

publisher = {Royal Society of Chemistry (RSC)},

abstract = {A phosphine-catalyzed method for the hydroboration of ynamides is reported. Boron adds to the beta carbon in acisfashion to yield (Z)-β-borylenamides.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Jacob2022c,

title = {A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides},

author = {Clément Jacob and Hajar Baguia and Amaury Dubart and Samuel Oger and Pierre Thilmany and Jérôme Beaudelot and Christopher Deldaele and Stefano Peruško and Yohann Landrain and Bastien Michelet and Samuel Neale and Eugénie Romero and Cécile Moucheron and Veronique Van Speybroeck and Cédric Theunissen and Gwilherm Evano},

doi = {10.1038/s41467-022-28098-x},

issn = {2041-1723},

year  = {2022},

date = {2022-12-00},

journal = {Nat Commun},

volume = {13},

number = {1},

publisher = {Springer Science and Business Media LLC},

abstract = {AbstractA general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, useful building blocks in natural product synthesis and medicinal chemistry, with full control of the regioselectivity of the cyclization resulting from a unique and underrated radical 4-exo-dig pathway.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Beaudelot2022d,

title = {Photoactive Copper Complexes: Properties and Applications},

author = {Jérôme Beaudelot and Samuel Oger and Stefano Peruško and Tuan-Anh Phan and Titouan Teunens and Cécile Moucheron and Gwilherm Evano},

doi = {10.1021/acs.chemrev.2c00033},

issn = {1520-6890},

year  = {2022},

date = {2022-11-23},

journal = {Chem. Rev.},

volume = {122},

number = {22},

pages = {16365--16609},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{DeSmet2022d,

title = {Selective Nickel‐Catalyzed Hydrodeacetoxylation of Aryl Acetates},

author = {Gilles De Smet and Xingfeng Bai and Carl Mensch and Sergey Sergeyev and Gwilherm Evano and Bert U. W. Maes},

doi = {10.1002/anie.202201751},

issn = {1521-3773},

year  = {2022},

date = {2022-09-19},

journal = {Angew Chem Int Ed},

volume = {61},

number = {38},

publisher = {Wiley},

abstract = {AbstractAcetate serves as a renewable and easily installed leaving group for selective deoxygenation of phenolics (ArOH). Ni‐catalyzed hydrodeacetoxylation of aryl acetates (Ar−OAc) with HBpin in a green carbonate solvent selectively delivers the corresponding deoxygenated arenes (ArH). The method is also applicable to highly challenging guaiacyl and syringyl acetates, leaving −OMe groups intact without arene reduction. Renewable 4‐propylguaiacol obtained from pine can also be transformed without significant loss in yield versus oil derived feedstock. The observed chemoselectivity for Ar−OAc versus ArO−Ac bond cleavage was rationalized based on mechanistic experiments and DFT calculations. ArOH side‐product formation is attributed to direct competitive Ni‐catalyzed reduction of the C=O bond. Hydrodeacyloxylation of a set of aryl alkanoates featured interesting chemoselectivity with a dramatic influence of the length and structure of the alkyl chain on catalysis.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Baguia2022g,

title = {Photoinduced, copper-catalysed direct perfluoroalkylation of heteroarenes},

author = {Hajar Baguia and Jérôme Beaudelot and Cécile Moucheron and Gwilherm Evano},

doi = {10.1039/d2cc02146c},

issn = {1364-548X},

year  = {2022},

date = {2022-08-11},

journal = {Chem. Commun.},

volume = {58},

number = {65},

pages = {9080--9083},

publisher = {Royal Society of Chemistry (RSC)},

abstract = {An efficient and general process is reported for the room temperature photoinduced, copper-catalysed direct perfluoroalkylation of a broad range of heteroarenes with commercially available perfluoroalkyl iodides.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Ling2022d,

title = {Copper‐Catalyzed Carbonylative Cross‐Coupling of Alkyl Iodides and Amines},

author = {Johanne Ling and Antoine Bruneau‐Voisine and Guillaume Journot and Gwilherm Evano},

doi = {10.1002/chem.202201356},

issn = {1521-3765},

year  = {2022},

date = {2022-08-04},

journal = {Chemistry A European J},

volume = {28},

number = {44},

publisher = {Wiley},

abstract = {AbstractA general copper‐catalyzed carbonylative cross‐coupling between amines and alkyl iodides is reported. Using a simple combination of catalytic amounts of copper(I) chloride andN,N,N’,N”,N”‐pentamethyldiethylenetriamine in the presence of sodium hydroxide under carbon monoxide pressure, a broad range of alkyl iodides and amines can be efficiently coupled to the corresponding amides that are obtained in good to excellent yields. Notable features of this process – the first one relying on a base metal catalyst – include the availability and low cost of the catalytic system, its successful use with primary, secondary, tertiary alkyl iodides and all classes of amines – with no or limited competing nucleophilic substitution without CO incorporation – as well as its efficiency with complex alkyl iodides and amines. Mechanistic studies demonstrated that a radical pathway is operative and the key role of CO.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Baguia2022h,

title = {Direct Perfluoroalkylation of C−H Bonds in (Hetero)arenes},

author = {Hajar Baguia and Gwilherm Evano},

doi = {10.1002/chem.202200975},

issn = {1521-3765},

year  = {2022},

date = {2022-07-20},

journal = {Chemistry A European J},

volume = {28},

number = {41},

publisher = {Wiley},

abstract = {AbstractPerfluoroalkylated (hetero)arenes represent an extremely important family of molecules commonly utilized in many areas such as medicinal chemistry, agrochemistry and material sciences. Due to their unique properties, they have attracted significant interest from synthetic chemists and various methods have been developed for their synthesis. Among them, the direct perfluoroalkylation of C(sp2)−H bonds in (hetero)arenes is one of the most attractive and straightforward ones, provided that it proceeds with high levels of regioselectivity. In this review article, a comprehensive overview of advances in this field is presented, with a special focus on the reaction mechanisms involved in these transformations and their regioselectivity. All methods available have been classified according to the nature of the perfluoroalkyl chain introduced, trifluoromethylation reactions being overviewed in a separate section, and to the nature of the reagents/catalysts required.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Siragusa2022g,

title = {Catalyst-Free Approach for the Degradation of Bio- and CO_{2}-Sourced Polycarbonates: A Step toward a Circular Plastic Economy},

author = {Fabiana Siragusa and Thomas Habets and Raphael Méreau and Gwilherm Evano and Bruno Grignard and Christophe Detrembleur},

doi = {10.1021/acssuschemeng.2c01891},

issn = {2168-0485},

year  = {2022},

date = {2022-07-11},

journal = {ACS Sustainable Chem. Eng.},

volume = {10},

number = {27},

pages = {8863--8875},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Siragusa2022h,

title = {Unifying Step-Growth Polymerization and On-Demand Cascade Ring-Closure Depolymerization via Polymer Skeletal Editing},

author = {Fabiana Siragusa and Jeremy Demarteau and Thomas Habets and Ion Olazabal and Koen Robeyns and Gwilherm Evano and Raphael Mereau and Thierry Tassaing and Bruno Grignard and Haritz Sardon and Christophe Detrembleur},

doi = {10.1021/acs.macromol.2c00696},

issn = {1520-5835},

year  = {2022},

date = {2022-06-14},

journal = {Macromolecules},

volume = {55},

number = {11},

pages = {4637--4646},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Thilmany2021d,

title = {Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides},

author = {Pierre Thilmany and Alejandro Guarnieri-Ibáñez and Clément Jacob and Jérôme Lacour and Gwilherm Evano},

doi = {10.1021/acsorginorgau.1c00021},

issn = {2694-247X},

year  = {2022},

date = {2022-02-02},

journal = {ACS Org. Inorg. Au},

volume = {2},

number = {1},

pages = {53--58},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Baguia2021d,

title = {Copper‐Catalyzed Direct Perfluoroalkylation of Heteroarenes},

author = {Hajar Baguia and Gwilherm Evano},

doi = {10.1002/chem.202103599},

issn = {1521-3765},

year  = {2022},

date = {2022-01-27},

journal = {Chemistry A European J},

volume = {28},

number = {6},

publisher = {Wiley},

abstract = {AbstractAn efficient and broadly applicable process is reported for the copper‐catalyzed direct perfluoroalkylation of C−H bonds in heteroarenes with commercially available perfluoroalkyl iodides. This reaction is based on a simple combination of copper(I) iodide and 1,10‐phenanthroline enabling the easy reduction of perfluoroalkyl iodides to the corresponding radical species that add to a wide range of heteroarenes including benzofurans, benzothiophenes, (aza)indoles, furans and pyrroles. High levels of regioselectivity were obtained in all cases and the efficiency and robustness of this process was highlighted by the direct perfluoroalkylation of furan‐containing peptides.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Dewez2021d,

title = {Ring-closing metathesis of \textit{N}-alkenyl-cyanamides},

author = {Damien F. Dewez and Christina Diacofotaki and Gwilherm Evano},

doi = {10.1039/d1qo01416a},

issn = {2052-4129},

year  = {2021},

date = {2021-11-23},

journal = {Org. Chem. Front.},

volume = {8},

number = {23},

pages = {6699--6703},

publisher = {Royal Society of Chemistry (RSC)},

abstract = {An entry to new classes of nitrogen-containing heterocycles featuring both a cyanamide and an unsaturated 5-, 6- or 7-membered ring is reported by RCM of the corresponding N-alkenyl-cyanamides, new partners for olefin metathesis.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Dubart2021d,

title = {Divergent Synthesis of α-Fluorinated Carbonyl and Carboxyl Derivatives by Double Electrophilic Activation of Amides},

author = {Amaury Dubart and Gwilherm Evano},

doi = {10.1021/acs.orglett.1c03450},

issn = {1523-7052},

year  = {2021},

date = {2021-11-19},

journal = {Org. Lett.},

volume = {23},

number = {22},

pages = {8931--8936},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Jacob2021d,

title = {Transient Directing Groups in Metal−Organic Cooperative Catalysis},

author = {Clément Jacob and Bert U. W. Maes and Gwilherm Evano},

doi = {10.1002/chem.202101598},

issn = {1521-3765},

year  = {2021},

date = {2021-10-07},

journal = {Chemistry A European J},

volume = {27},

number = {56},

pages = {13899--13952},

publisher = {Wiley},

abstract = {AbstractThe direct functionalization of C−H bonds is among the most fundamental chemical transformations in organic synthesis. However, when the innate reactivity of the substrate cannot be utilized for the functionalization of a given single C−H bond, this selective C−H bond functionalization mostly relies on the use of directing groups that allow bringing the catalyst in close proximity to the C−H bond to be activated and these directing groups need to be installed before and cleaved after the transformation, which involves two additional undesired synthetic operations. These additional steps dramatically reduce the overall impact and the attractiveness of C−H bond functionalization techniques since classical approaches based on substrate pre‐functionalization are sometimes still more straightforward and appealing. During the past decade, a different approach involving both the in situ installation and removal of the directing group, which can then often be used in a catalytic manner, has emerged: the transient directing group strategy. In addition to its innovative character, this strategy has brought C−H bond functionalization to an unprecedented level of usefulness and has enabled the development of remarkably efficient processes for the direct and selective introduction of functional groups onto both aromatic and aliphatic substrates. The processes unlocked by the development of these transient directing groups will be comprehensively overviewed in this review article.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Biswas2021d,

title = {Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis},

author = {Sovan Biswas and Ben F. Van Steijvoort and Marjo Waeterschoot and Narendraprasad Reddy Bheemireddy and Gwilherm Evano and Bert U. W. Maes},

doi = {10.1002/anie.202106716},

issn = {1521-3773},

year  = {2021},

date = {2021-09-27},

journal = {Angew Chem Int Ed},

volume = {60},

number = {40},

pages = {21988--21996},

publisher = {Wiley},

abstract = {AbstractBridged nitrogen bicyclic skeletons have been accessed via unprecedented site‐ and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd‐catalyzed γ‐C(sp3)‐H olefination of aminocyclohexane with gem‐dibromoalkenes, followed by a consecutive intramolecular Cu‐catalyzed amidation of the 1‐bromo‐1‐alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza‐ and oxa‐analogues. The Cu catalyst of the Ullmann‐Goldberg reaction additionally avoids off‐cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7‐alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio‐ and diastereoselective Pd‐catalyzed γ‐C(sp3)‐H olefination is achieved.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Moucheron2021d,

title = {[Cu(bcp)(DPEphos)]+: A Versatile and Efficient Copper-Based Photoredox Catalyst and Photosensitizer},

author = {Cécile Moucheron and Gwilherm Evano and Samuel Oger and Hajar Baguia and Tuan-Anh Phan and Titouan Teunens and Jérôme Beaudelot},

doi = {10.1055/a-1504-6972},

issn = {2509-9396},

year  = {2021},

date = {2021-04-00},

journal = {SynOpen},

volume = {05},

number = {02},

pages = {141--144},

publisher = {Georg Thieme Verlag KG},

abstract = {Abstract},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Wakuluk-Machado2019d,

title = {Pd(OH)_{2}/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide},

author = {Anne-Marie Wakuluk-Machado and Damien F. Dewez and Hajar Baguia and Miguel Imbratta and Pierre-Georges Echeverria and Gwilherm Evano},

doi = {10.1021/acs.oprd.9b00402},

issn = {1520-586X},

year  = {2020},

date = {2020-05-15},

journal = {Org. Process Res. Dev.},

volume = {24},

number = {5},

pages = {713--723},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Thilmany2019d,

title = {Efficient and Divergent Synthesis of α‐Halogenated Amides and Esters by Double Electrophilic Activation of Ynamides},

author = {Pierre Thilmany and Gwilherm Evano},

doi = {10.1002/anie.201911722},

issn = {1521-3773},

year  = {2020},

date = {2020-01-02},

journal = {Angew Chem Int Ed},

volume = {59},

number = {1},

pages = {242--246},

publisher = {Wiley},

abstract = {AbstractAn efficient and modular entry to α‐halogenated amides and esters is reported. This reaction is based on an underestimated double electrophilic activation of ynamides sequentially involving highly reactive activated keteniminium and iminium ions. Upon simple reaction with HCl and an electrophilic halogenation reagent in the presence of water or an alcohol, a broad range of ynamides can be transformed, in a highly divergent manner, to α‐halo amides and esters with high efficiency and under mild conditions.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Nitelet2019c,

title = {Total Synthesis of Conulothiazole A},

author = {Antoine Nitelet and Phidéline Gérard and Jimmy Bouche and Gwilherm Evano},

doi = {10.1021/acs.orglett.9b01490},

issn = {1523-7052},

year  = {2019},

date = {2019-06-07},

journal = {Org. Lett.},

volume = {21},

number = {11},

pages = {4318--4321},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2019c,

title = {Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes},

author = {Gwilherm Evano and Cédric Theunissen},

doi = {10.1002/anie.201806629},

issn = {1521-3773},

year  = {2019},

date = {2019-05-27},

journal = {Angew Chem Int Ed},

volume = {58},

number = {22},

pages = {7202--7236},

publisher = {Wiley},

abstract = {AbstractAlkylation of arenes is one of the most fundamental transformations in chemical synthesis and leads to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel–Crafts reaction, radical additions, metalation, or prefunctionalization of the arene: these methods, however, suffer from limitations in scope, efficiency, and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group that facilitates, in the presence of a metal catalyst, the regioselective alkylation of a C−H bond. These directed alkylations of C−H bonds in arenes will be comprehensively summarized in this Review.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Thilmany2018d,

title = {Copper-Mediated N-Arylations of Hydantoins},

author = {Pierre Thilmany and Phidéline Gérard and Agathe Vanoost and Christopher Deldaele and Laurent Petit and Gwilherm Evano},

doi = {10.1021/acs.joc.8b02284},

issn = {1520-6904},

year  = {2019},

date = {2019-01-04},

journal = {J. Org. Chem.},

volume = {84},

number = {1},

pages = {392--400},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Nitelet2018c,

title = {Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing},

author = {Antoine Nitelet and Vanessa Kairouz and Hélène Lebel and André Charette and Gwilherm Evano},

doi = {10.1055/s-0037-1610398},

issn = {1437-210X},

year  = {2019},

date = {2019-01-00},

journal = {Synthesis},

volume = {51},

number = {01},

pages = {251--257},

publisher = {Georg Thieme Verlag KG},

abstract = {A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the double bond geometry. The reaction time was reduced by a factor of 24–48 compared to the batch process.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Baguia2019,

title = {[(DPEPhos)(bcp)Cu]PF_{6}: A General and Broadly Applicable Copper-Based Photoredox Catalyst},

author = {Hajar Baguia and Christopher Deldaele and Bastien Michelet and Jérôme Beaudelot and Cédric Theunissen and Cécile Moucheron and Gwilherm Evano},

doi = {10.3791/59739},

issn = {1940-087X},

year  = {2019},

date = {2019-00-00},

journal = {JoVE},

number = {147},

publisher = {MyJove Corporation},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Guissart2018c,

title = {Fishing with copper acetylides: Selective alkynylation of heteronucleophiles},

author = {Céline Guissart and Michel Luhmer and Gwilherm Evano},

doi = {10.1016/j.tet.2018.09.053},

issn = {0040-4020},

year  = {2018},

date = {2018-11-00},

journal = {Tetrahedron},

volume = {74},

number = {47},

pages = {6727--6736},

publisher = {Elsevier BV},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Deldaele2018b,

title = {A General Copper-based Photoredox Catalyst for Organic Synthesis: Scope, Application in Natural Product Synthesis and Mechanistic Insights},

author = {Christopher Deldaele and Bastien Michelet and Hajar Baguia and Sofia Kajouj and Eugenie Romero and Cecile Moucheron and Gwilherm Evano},

doi = {10.2533/chimia.2018.621},

issn = {2673-2424},

year  = {2018},

date = {2018-09-26},

journal = {Chimia},

volume = {72},

number = {9},

publisher = {Swiss Chemical Society},

abstract = {

        Organic transformations can broadly be classified into four categories including cationic, anionic, pericyclic and radical reactions. While the last category has been known for decades to provide remarkably efficient synthetic pathways, it has long been hampered by the need for toxic

 reagents, which considerably limited its impact on chemical synthesis. This situation has come to an end with the introduction of new concepts for the generation of radical species, photoredox catalysis – which simply relies on the use of a catalyst that can be activated upon visible

 light irradiation – certainly being the most efficient one. The state-of-the-art catalysts mostly rely on the use of ruthenium and iridium complexes and organic dyes, which still considerably limits their broad implementation in chemical processes: alternative readily available catalysts

 based on inexpensive, environmentally benign base metals are therefore strongly needed. Furthermore, expanding the toolbox of methods based on photoredox catalysis will facilitate the discovery of new light-mediated transformations. This article details the use of a simple copper complex which,

 upon activation with blue light, can initiate a broad range of radical reactions.

      },

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Guissart2018d,

title = {Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides},

author = {Céline Guissart and Andre Barros and Luis Rosa Barata and Gwilherm Evano},

doi = {10.1021/acs.orglett.8b01896},

issn = {1523-7052},

year  = {2018},

date = {2018-09-07},

journal = {Org. Lett.},

volume = {20},

number = {17},

pages = {5098--5102},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2018b,

title = {Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review},

author = {Gwilherm Evano and Antoine Nitelet and Pierre Thilmany and Damien F. Dewez},

doi = {10.3389/fchem.2018.00114},

issn = {2296-2646},

year  = {2018},

date = {2018-04-26},

journal = {Front. Chem.},

volume = {6},

publisher = {Frontiers Media SA},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Gerard2018b,

title = {Copper-Catalyzed Direct Oxidative α-Arylation of Pyrrolidine with Phenols and Naphtols},

author = {Phideline Gerard and Gwilherm Evano},

doi = {10.2174/1570178614666171120164418},

issn = {1570-1786},

year  = {2018},

date = {2018-04-12},

journal = {LOC},

volume = {15},

number = {5},

pages = {359--364},

publisher = {Bentham Science Publishers Ltd.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Foubelo2018,

title = {Editorial: Special Issue of Letters in Organic Chemistry in Honor of Prof. Miguel Yus},

author = {Francisco Foubelo and Gwilherm Evano},

doi = {10.2174/157017861505180412100627},

issn = {1570-1786},

year  = {2018},

date = {2018-04-12},

journal = {LOC},

volume = {15},

number = {5},

pages = {333--334},

publisher = {Bentham Science Publishers Ltd.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2017f,

title = {Editorial: Letters in Organic Chemistry - Where Now?},

author = {Gwilherm Evano},

doi = {10.2174/157017861501171211095813},

issn = {1570-1786},

year  = {2017},

date = {2017-12-11},

journal = {LOC},

volume = {15},

number = {1},

publisher = {Bentham Science Publishers Ltd.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Nitelet2017b,

title = {Copper-Catalyzed Alkenylation of Cyanamides},

author = {Antoine Nitelet and Johan Wouters and Damien F. Dewez and Gwilherm Evano},

doi = {10.1021/acs.orglett.7b02859},

issn = {1523-7052},

year  = {2017},

date = {2017-12-01},

journal = {Org. Lett.},

volume = {19},

number = {23},

pages = {6276--6279},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Lecomte2017b,

title = {Aryl Ynol Ethers: Stable, Readily Available and Useful Precursors of Highly Reactive Ketenium Ions},

author = {Morgan Lecomte and Gwilherm Evano},

doi = {10.2174/1570178614666170608125358},

issn = {1570-1786},

year  = {2017},

date = {2017-08-22},

journal = {LOC},

volume = {14},

number = {8},

publisher = {Bentham Science Publishers Ltd.},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2017,

title = {Keteniminium Ions: Unique and Versatile Reactive Intermediates for Chemical Synthesis},

author = {Gwilherm Evano and Morgan Lecomte and Pierre Thilmany and Cédric Theunissen},

doi = {10.1055/s-0036-1588452},

issn = {1437-210X},

year  = {2017},

date = {2017-08-00},

journal = {Synthesis},

volume = {49},

number = {15},

pages = {3183--3214},

publisher = {Georg Thieme Verlag KG},

abstract = {Keteniminium ions have been demonstrated to be remarkably useful and versatile reactive intermediates in chemical synthesis. These unique heterocumulenes are pivotal electrophilic species involved in a number of efficient and selective transformations. More recently, even more reactive ‘activated’ keteniminium ions bearing an additional electron-withdrawing group on the nitrogen atom have been extensively investigated. The chemistry of these unique reactive intermediates, including representative methods for their in situ generation, will be overviewed in this review article.1 	Introduction2 	The Chemistry of Keteniminium Ions3 	The Chemistry of Activated Keteniminium Ions4 	Keteniminium Ions: Pivotal Intermediates for the Synthesis of Natural and/or Biologically Relevant Molecules5 	Conclusions and Perspectives},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Michelet2017b,

title = {A General Copper Catalyst for Photoredox Transformations of Organic Halides},

author = {Bastien Michelet and Christopher Deldaele and Sofia Kajouj and Cécile Moucheron and Gwilherm Evano},

doi = {10.1021/acs.orglett.7b01518},

issn = {1523-7052},

year  = {2017},

date = {2017-07-07},

journal = {Org. Lett.},

volume = {19},

number = {13},

pages = {3576--3579},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2017i,

title = {The anionic chemistry of ynamides: A review},

author = {Gwilherm Evano and Bastien Michelet and Chunyang Zhang},

doi = {10.1016/j.crci.2016.12.002},

issn = {1631-0748},

year  = {2017},

date = {2017-06-00},

journal = {Comptes Rendus Chimie},

volume = {20},

number = {6},

pages = {648--664},

publisher = {Cellule MathDoc/Centre Mersenne},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Theunissen2017,

title = {Cationic polycyclization of ynamides: building up molecular complexity},

author = {Cédric Theunissen and Benoît Métayer and Morgan Lecomte and Nicolas Henry and Hwai-Chien Chan and Guillaume Compain and Phidéline Gérard and Christian Bachmann and Naima Mokhtari and Jérome Marrot and Agnès Martin-Mingot and Sébastien Thibaudeau and Gwilherm Evano},

doi = {10.1039/c7ob00850c},

issn = {1477-0539},

year  = {2017},

date = {2017-00-00},

journal = {Org. Biomol. Chem.},

volume = {15},

number = {20},

pages = {4399--4416},

publisher = {Royal Society of Chemistry (RSC)},

abstract = {
Simple activation of readily available ynamides under acidic conditions triggers an unprecedented cationic polycyclization yielding highly substituted polycyclic nitrogen heterocycles.
},

keywords = {},

pubstate = {published},

tppubtype = {article}

}