Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 49, Pages 14915-14919Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507844
Keywords
electronic properties; gold; homogeneous catalysis; N-heterocyclic carbenes; rhodium
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Funding
- NSFC [21202128, 21572175]
- DOE [DEFG02-13ER16370]
- China Scholarship Council
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Cyclic (amino)(aryl) carbenes (CAArCs) result from the replacement of the alkyl substituent of cyclic (alkyl)(amino) carbenes (CAACs) by an aryl group. This structural modification leads to enhanced electrophilicity of the carbene center with retention of the high nucleophilicity of CAACs, and therefore CAArCs feature a small singlet-triplet gap. The isoindolium precursors are readily prepared in good yields, and deprotonation at low temperature, in the presence of [RhCl(cod)](2) and [(Me2S) AuCl] lead to air-stable rhodium and gold CAArC-supported complexes, respectively. The rhodium complexes promote the [3+2] cycloaddition of diphenylcyclopropenone with ethyl phenylpropiolate, and induce the addition of 2-vinylpyridine to alkenes by CH activation. The gold complexes allow for the catalytic three-component preparation of 1,2-dihydroquinolines from aniline and phenyl acetylene. These preliminary results illustrate the potential of CAArC ligands in transition-metal catalysis.
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