镍催化 Boc 活化的芳胺通过非定向选择性芳基 C-N 键断裂的 Kumada 偶联反应。
Nickel-Catalyzed Kumada Coupling of Boc-Activated Aromatic Amines via Nondirected Selective Aryl C-N Bond Cleavage.
机构信息
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP) , University of Chinese Academy of Sciences, Chinese Academy of Sciences , Lanzhou 730000 , China.
Department of Chemistry , Zhejiang University , Hangzhou 310027 , China.
出版信息
Org Lett. 2019 Feb 15;21(4):1226-1231. doi: 10.1021/acs.orglett.9b00242. Epub 2019 Jan 31.
A nickel-catalyzed Kumada coupling of aniline derivatives was developed by selective cleavage of aryl C-N bonds under mild reaction conditions. Without preinstallation of an ortho directing group on anilines, the cross-coupling reactions of Boc-protected aromatic amines with aryl Grignard reagents afforded unsymmetric biaryls. Mechanistic studies by DFT calculations revealed that the nickel-mediated C-N bond cleavage is the rate-limiting step.
发展了一种镍催化的苯胺衍生物的 Kumada 偶联反应，通过在温和的反应条件下选择性断裂芳基 C-N 键实现。在苯胺上无需预先安装邻位导向基团的情况下，Boc 保护的芳基胺与芳基格氏试剂的交叉偶联反应得到了不对称联苯。通过 DFT 计算的机理研究表明，镍介导的 C-N 键断裂是速率限制步骤。
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