Carbon–carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation†

Received: 14 Feb 2021, Revised: 16 Feb 2021, Accepted: 10 June 2021, Available online: 18 June 2021, Version of Record: 18 June 2021

Li Wang,‡ab Qi Zhong,‡ab Youliang Zou,b Youzhi Yin,b Aizhen Wu,b Quan Chen,b Ke Zhang,b Jiachen Jiang,b Mengzhen Zhaob and Hua Zhang *ab

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* Corresponding authors
a Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education, Hubei Key Laboratory of Catalysis and Materials Science, South-Central University for Nationalities, Wuhan 430074, China
E-mail: huazhang@scuec.edu.cn
b College of Chemistry, Nanchang University, Nanchang 330031, China

Abstract


Selective carbon–carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2–Csp3 and Csp2–Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C–C bond activation to afford two C–B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C–B bond formation and C–C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C–C bond activation.
Graphical abstract: Carbon–carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation



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