Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 24, Pages 7977-7981Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901090
Keywords
atom-economical reactions; gold; homogeneous catalysis; N-heterocyclic carbenes; organometallic complexes
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Funding
- Agence Nationale de Recherche [ANR-16-CE07-0006]
- Centre National de la Recherche Scientifique (CNRS)
- University Cote d'Azur
- ANR
- Agence Nationale de la Recherche (ANR) [ANR-16-CE07-0006] Funding Source: Agence Nationale de la Recherche (ANR)
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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).
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