Yi Mingjun, Wu Xiaoyu, Yang Liqun, Yuan Yao, Lu Yan, Zhang Zhaoguo
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
J Org Chem. 2024 Sep 6;89(17):12583-12590. doi: 10.1021/acs.joc.4c01510. Epub 2024 Aug 19.
A protocol induced by visible light for the direct insertion of α-carbonyl carbenes into the B-H bond of amine-borane adducts has been developed under conditions that are free of metal and photocatalyst. This approach provides a straightforward route to various organoboron compounds from diazo compounds and amine-borane adducts with moderate to good yields. Mechanistic investigations reveal that this photoinduced reaction proceeds through concerted carbene insertion into the B-H bond, and the photoinduced generation of free carbene from α-diazo esters may be the rate-determining step.
在无金属和光催化剂的条件下，开发了一种由可见光诱导的将α-羰基卡宾直接插入胺硼烷加合物B-H键的反应方案。该方法为从重氮化合物和胺硼烷加合物制备各种有机硼化合物提供了一条直接的途径，产率适中至良好。机理研究表明，该光诱导反应通过卡宾协同插入B-H键进行，α-重氮酯光诱导生成游离卡宾可能是速率决定步骤。
