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镍介导的通过碳-碳键断裂的简单未应变酮的脱羰反应。

Nickel-Mediated Decarbonylation of Simple Unstrained Ketones through the Cleavage of Carbon-Carbon Bonds.

机构信息

Department of Applied Chemistry, Faculty of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

出版信息

J Am Chem Soc. 2017 Feb 1;139(4):1416-1419. doi: 10.1021/jacs.6b12293. Epub 2017 Jan 23.

DOI:10.1021/jacs.6b12293
PMID:28099004
Abstract

Despite advances in methods for the decarbonylation of aldehydes, the decarbonylation of ketones has been met with limited success because this process requires the activation of two inert carbon-carbon bonds. All of the decarbonylation reactions of simple unstrained ketones reported to date require the addition of a stoichiometric rhodium complex. We report herein the nickel/N-heterocyclic carbene-mediated decarbonylation of simple diaryl ketones. This reaction shows unique acceleration effects based on the presence of both electron-donating and electron-withdrawing groups.

摘要

尽管在醛的脱羰方法方面取得了进展,但酮的脱羰反应却收效甚微,因为该过程需要激活两个惰性的碳-碳键。迄今为止,所有已报道的简单无张力酮的脱羰反应都需要加入化学计量的铑络合物。在此,我们报告了镍/N-杂环卡宾介导的简单二芳基酮的脱羰反应。该反应显示出基于供电子和吸电子基团的存在而具有独特的加速效应。

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