An Original L-shape, Tunable N-Heterocyclic Carbene Platform for Efficient Gold(I) Catalysis

• Published in: Angewandte Chemie International Edition
• Main Authors: Tang, Yue, Benaissa, Idir, Huynh, Mathieu, Vendier, Laure, Lugan, Noël, Bastin, Stéphanie, Belmont, Philippe, César, Vincent, Michelet, Véronique
• Other Authors: Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris Sciences et Lettres (PSL), Institut de Chimie de Nice (ICN), Université Nice Sophia Antipolis (1965 - 2019) (UNS)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université Côte d'Azur (UniCA), Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Faculté de Pharmacie de Paris - Université Paris Descartes (UPD5 Pharmacie), Université Paris Descartes - Paris 5 (UPD5), CNRS, Université Côte d'Azur, ANR-16-CE07-0006,GOLDWAR,Catalyse asymétrique en présence de complexes d'or(I) et d'or(III) – Un nouvel arsenal pour la construction d'architectures moléculaires chirales(2016)
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2019
• Subjects: [CHIM.COOR]Chemical Sciences/Coordination chemistry; [CHIM.CATA]Chemical Sciences/Catalysis; [CHIM.ORGA]Chemical Sciences/Organic chemistry; IPY
• Online Access: https://hal.science/hal-02335228; https://hal.science/hal-02335228/document; https://hal.science/hal-02335228/file/Angew%20Chem%20int%20Ed,%202019,%2058,%207977.pdf; https://doi.org/10.1002/anie.201901090

International audience 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.