Synthesis of Hemilabile Cyclic (Alkyl)(amino)carbenes (CAACs) and Applications in Organometallic Chemistry

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• 作者：Jiaxiang Chu ; Dominik Munz ; Rodolphe Jazzar ; Mohand Melaimi ; Guy Bertrand
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：June 29, 2016
• 年：2016
• 卷：138
• 期：25
• 页码：7884-7887
• 全文大小：310K
• 年卷期：0
• ISSN：1520-5126

文摘

A versatile methodology, involving readily available starting materials, allows for the synthesis of stable hemilabile bidentate cyclic (alkyl)(amino)carbenes (CAACs) featuring alkene, ether, amine, imine, and phosphine functionalities. The stability of the free carbenes has been exploited for the synthesis of copper(I) and gold(I) complexes. It is shown that the pendant imine moiety stabilizes the gold(III) oxidation state and enables the C–C bond oxidative addition of biphenylene to the corresponding cationic gold(I) complex. The latter and the corresponding copper(I) complex show high catalytic activity for the hydroarylation of α-methylstyrene with N,N-dimethylaniline, and the copper(I) complex promotes the anti-Markovnikov hydrohydrazination of phenyl acetylene with high selectivity.