An Original L‐shape, Tunable N‐Heterocyclic Carbene Platform for Efficient Gold(I) Catalysis
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....
Published in: | Angewandte Chemie |
---|---|
Main Authors: | , , , , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2019
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/ange.201901090 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ange.201901090 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ange.201901090 |
Summary: | 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 5 Me complex is remarkable and mostly arises from a combination of steric protection and stabilization of the cationic Au I active species by ligand 1 Me . |
---|