@article{Jacob2025d,

title = {Photoredox-Catalyzed Reductive Activation of Ammonium Salts},

author = {Clément Jacob and Julien Annibaletto and Cédric Theunissen},

doi = {10.1055/a-2572-0881},

issn = {1437-2096},

year  = {2025},

date = {2025-07-00},

urldate = {2025-07-00},

journal = {Synlett},

volume = {36},

number = {12},

pages = {1729--1734},

publisher = {Georg Thieme Verlag KG},

abstract = {<jats:title>Abstract</jats:title><jats:p>The reductive activation of C–N bonds by single-electron transfer enables the generation of radicals from readily available and abundant amines. Despite their potential, such transformations remain challenging because of the stability of the C–N bond, which often requires preactivation to facilitate its cleavage. In this context, quaternary ammonium salts constitute ideal amine-derived radical precursors as they are stable and easy to handle, in addition to enabling the design of atom-economical processes. In this article, we highlight our recent work on the photoredox-catalyzed reductive activation of ammonium salts. Several ammonium salts could indeed be successfully activated using iridium photoredox catalysis, the corresponding radicals being subsequently engaged in hydrodeamination reactions and radical couplings. Moreover, the reactivity observed experimentally could be correlated to the redox potentials of the ammonium salts, which were determined by cyclic voltammetry.</jats:p><jats:p>1 	Introduction</jats:p><jats:p>2 	Hydrodeamination of Benzylic and Aryl Ammonium Salts</jats:p><jats:p>3 	Selective Activation and Extension to Radical Couplings</jats:p><jats:p>4 	Determination of the Redox Potentials of Ammonium Salts</jats:p><jats:p>5 	Conclusion</jats:p>},

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{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{Annibaletto2022c,

title = {Ammonium Salts as Convenient Radical Precursors Using Iridium Photoredox Catalysis},

author = {Julien Annibaletto and Clément Jacob and Cédric Theunissen},

doi = {10.1021/acs.orglett.2c01407},

issn = {1523-7052},

year  = {2022},

date = {2022-06-17},

journal = {Org. Lett.},

volume = {24},

number = {23},

pages = {4170--4175},

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{Theunissen2019b,

title = {Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis},

author = {Cédric Theunissen and Melissa A. Ashley and Tomislav Rovis},

doi = {10.1021/jacs.8b13663},

issn = {1520-5126},

year  = {2019},

date = {2019-05-01},

journal = {J. Am. Chem. Soc.},

volume = {141},

number = {17},

pages = {6791--6796},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Theunissen2019,

title = {Discussion Addendum for: Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide},

author = {Cédric Theunissen},

doi = {10.15227/orgsyn.096.0195},

issn = {2333-3553},

year  = {2019},

date = {2019-00-00},

journal = {Org. Synth.},

volume = {96},

pages = {195--213},

publisher = {Organic Syntheses},

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{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{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}

}

@article{Theunissen2017b,

title = {Copper-catalyzed direct alkylation of heteroarenes},

author = {Cédric Theunissen and Jianjun Wang and Gwilherm Evano},

doi = {10.1039/c6sc05622a},

issn = {2041-6539},

year  = {2017},

date = {2017-00-00},

journal = {Chem. Sci.},

volume = {8},

number = {5},

pages = {3465--3470},

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

abstract = {
An efficient and broadly applicable process is reported for the direct alkylation of heteroarene C–H bonds, based on the copper-catalyzed addition of alkyl radicals generated from activated secondary and tertiary alkyl bromides to a range of arenes, and their benzo-fused derivatives.
},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2016,

title = {A Journey in the Chemistry of Ynamides: From Synthesis to Applications},

author = {Gwilherm Evano and Nicolas Blanchard and Guillaume Compain and Alexis Coste and Charles S. Demmer and Wafa Gati and Céline Guissart and Jérémy Heimburger and Nicolas Henry and Kévin Jouvin and Ganesan Karthikeyan and Anouar Laouiti and Morgan Lecomte and Agnès Martin-Mingot and Benoît Métayer and Bastien Michelet and Antoine Nitelet and Cédric Theunissen and Sébastien Thibaudeau and Jianjun Wang and Maxence Zarca and Chunyang Zhang},

doi = {10.1246/cl.160260},

issn = {1348-0715},

year  = {2016},

date = {2016-06-05},

journal = {Chem. Lett.},

volume = {45},

number = {6},

pages = {574--585},

publisher = {Oxford University Press (OUP)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Theunissen2014b,

title = {Keteniminium Ion-Initiated Cascade Cationic Polycyclization},

author = {Cédric Theunissen and Benoît Métayer and Nicolas Henry and Guillaume Compain and Jérome Marrot and Agnès Martin-Mingot and Sébastien Thibaudeau and Gwilherm Evano},

doi = {10.1021/ja504818p},

issn = {1520-5126},

year  = {2014},

date = {2014-09-10},

journal = {J. Am. Chem. Soc.},

volume = {136},

number = {36},

pages = {12528--12531},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Theunissen2014,

title = {Room-Temperature Direct Alkynylation of Arenes with Copper Acetylides},

author = {Cédric Theunissen and Gwilherm Evano},

doi = {10.1021/ol502030y},

issn = {1523-7052},

year  = {2014},

date = {2014-09-05},

journal = {Org. Lett.},

volume = {16},

number = {17},

pages = {4488--4491},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2014b,

title = {Convenient and Practical Alkynylation of Heteronucleophiles with Copper Acetylides},

author = {Gwilherm Evano and Cédric Theunissen and Morgan Lecomte and Kévin Jouvin and Anouar Laouiti and Céline Guissart and Jérémy Heimburger and Estelle Loire},

doi = {10.1055/s-0033-1341025},

issn = {1437-210X},

year  = {2014},

date = {2014-04-22},

journal = {Synthesis},

volume = {46},

number = {09},

pages = {1157--1166},

publisher = {Georg Thieme Verlag KG},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2014c,

title = {Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes},

author = {Gwilherm Evano and Annie-Claude Gaumont and Carole Alayrac and Iwona E. Wrona and Joshua R. Giguere and Olivier Delacroix and Alexandre Bayle and Kévin Jouvin and Cédric Theunissen and Jérémie Gatignol and Andrew C. Silvanus},

doi = {10.1016/j.tet.2013.11.073},

issn = {0040-4020},

year  = {2014},

date = {2014-02-00},

journal = {Tetrahedron},

volume = {70},

number = {8},

pages = {1529--1616},

publisher = {Elsevier BV},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2014,

title = {Turning unreactive copper acetylides into remarkably powerful and mild alkyne transfer reagents by oxidative umpolung},

author = {G. Evano and K. Jouvin and C. Theunissen and C. Guissart and A. Laouiti and C. Tresse and J. Heimburger and Y. Bouhoute and R. Veillard and M. Lecomte and A. Nitelet and S. Schweizer and N. Blanchard and C. Alayrac and A.-C. Gaumont},

doi = {10.1039/c4cc03198a},

issn = {1364-548X},

year  = {2014},

date = {2014-00-00},

journal = {Chem. Commun.},

volume = {50},

number = {70},

pages = {10008--10018},

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

abstract = {
Upon oxidation, copper acetylides formally behave as highly electrophilic species that could be trapped by a wide range of nucleophiles.
},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Jouvin2013,

title = {Unprecedented Synthesis of Alkynylphosphine-boranes through Room-Temperature Oxidative Alkynylation},

author = {Kévin Jouvin and Romain Veillard and Cédric Theunissen and Carole Alayrac and Annie-Claude Gaumont and Gwilherm Evano},

doi = {10.1021/ol402197d},

issn = {1523-7052},

year  = {2013},

date = {2013-09-06},

journal = {Org. Lett.},

volume = {15},

number = {17},

pages = {4592--4595},

publisher = {American Chemical Society (ACS)},

keywords = {},

pubstate = {published},

tppubtype = {article}

}

@article{Evano2013,

title = {Impact of copper-catalyzed cross-coupling reactions in natural product synthesis: the emergence of new retrosynthetic paradigms},

author = {Gwilherm Evano and Cédric Theunissen and Alexandre Pradal},

doi = {10.1039/c3np70071b},

issn = {1460-4752},

year  = {2013},

date = {2013-00-00},

journal = {Nat. Prod. Rep.},

volume = {30},

number = {12},

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

keywords = {},

pubstate = {published},

tppubtype = {article}

}