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

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.

SUBMITTER: Wang L

PROVIDER: S-EPMC8612372 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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

Wang Li L Zhong Qi Q Zou Youliang Y Yin Youzhi Y Wu Aizhen A Chen Quan Q Zhang Ke K Jiang Jiachen J Zhao Mengzhen M Zhang Hua H

Chemical science 20211102 45

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. Prelimin ...[more]

PMID: 34909151

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