An Original L-shape, Tunable N-Heterocyclic Carbene Platform for Efficient Gold(I) Catalysis
Yue Tang
PSL Research University, Chimie ParisTech—CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
University Côte d'Azur, Institut de Chimie de Nice, UMR 7272 CNRS, Parc Valrose, Faculté des Sciences, 06100 Nice, France
These authors contributed equally to this work.
Search for more papers by this authorIdir Benaissa
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
These authors contributed equally to this work.
Search for more papers by this authorMathieu Huynh
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorDr. Laure Vendier
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorDr. Noël Lugan
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorCorresponding Author
Dr. Stéphanie Bastin
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorProf. Philippe Belmont
Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8038 CiTCoM, 4 avenue de l'Observatoire, 75006 Paris, France
Search for more papers by this authorCorresponding Author
Dr. Vincent César
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorCorresponding Author
Prof. Véronique Michelet
PSL Research University, Chimie ParisTech—CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
University Côte d'Azur, Institut de Chimie de Nice, UMR 7272 CNRS, Parc Valrose, Faculté des Sciences, 06100 Nice, France
Search for more papers by this authorYue Tang
PSL Research University, Chimie ParisTech—CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
University Côte d'Azur, Institut de Chimie de Nice, UMR 7272 CNRS, Parc Valrose, Faculté des Sciences, 06100 Nice, France
These authors contributed equally to this work.
Search for more papers by this authorIdir Benaissa
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
These authors contributed equally to this work.
Search for more papers by this authorMathieu Huynh
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorDr. Laure Vendier
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorDr. Noël Lugan
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorCorresponding Author
Dr. Stéphanie Bastin
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorProf. Philippe Belmont
Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8038 CiTCoM, 4 avenue de l'Observatoire, 75006 Paris, France
Search for more papers by this authorCorresponding Author
Dr. Vincent César
LCC-CNRS, Université de Toulouse, CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Search for more papers by this authorCorresponding Author
Prof. Véronique Michelet
PSL Research University, Chimie ParisTech—CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
University Côte d'Azur, Institut de Chimie de Nice, UMR 7272 CNRS, Parc Valrose, Faculté des Sciences, 06100 Nice, France
Search for more papers by this authorIn memory of Guy Lavigne
Abstract
The synthesis and characterization of original NHC ligands based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) scaffold functionalized with a flanking barbituric heterocycle is described as well as their use as tunable ligands for efficient gold-catalyzed C−N, C−O, and C−C bond formations. High activity, regio-, chemo-, and stereoselectivities are obtained for hydroelementation and domino processes, underlining the excellent performance (TONs and TOFs) of these IPy-based ligands in gold catalysis. The gold-catalyzed domino reactions of 1,6-enynes give rise to functionalized heterocycles in excellent isolated yields under mild conditions. The efficiency of the NHC gold 5Me complex is remarkable and mostly arises from a combination of steric protection and stabilization of the cationic AuI active species by ligand 1Me.
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