4.8 Article

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

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 24, 页码 7977-7981

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901090

关键词

atom-economical reactions; gold; homogeneous catalysis; N-heterocyclic carbenes; organometallic complexes

资金

  1. Agence Nationale de Recherche [ANR-16-CE07-0006]
  2. Centre National de la Recherche Scientifique (CNRS)
  3. University Cote d'Azur
  4. ANR
  5. Agence Nationale de la Recherche (ANR) [ANR-16-CE07-0006] Funding Source: Agence Nationale de la Recherche (ANR)

向作者/读者索取更多资源

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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