Catalyst-free benzylic C(sp3)–H cross-coupling with organotrifluoroborates enabled by electrochemistry

Chao Li; Ran Ding; Heng-Yi Guo; Shuang Xia; Lei Shu; Pei-Long Wang; Hongji Li

doi:10.1039/D2GC02204D

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Catalyst-free benzylic C(sp³)–H cross-coupling with organotrifluoroborates enabled by electrochemistry†

Chao Li,^a Ran Ding,

^ac Heng-Yi Guo,^b Shuang Xia,^b Lei Shu,^a Pei-Long Wang

*^ab and Hongji Li

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
E-mail: wangpl@chnu.edu.cn, hongjili@chnu.edu.cn

^b Information College, Huaibei Normal University, Huaibei 235000, China

^c College of Chemistry and Materials Engineering, Anhui Science and Technology University, Bengbu, Anhui, P. R. China

Abstract

Herein, we report a rare catalyst-free electrochemical cross-coupling of benzylic C–H bonds with organotrifluoroborates, which readily proceeds at room temperature and provides a unique protocol for forging C(sp³)–C(sp³), C(sp³)–C(sp²) and C(sp³)–C(sp) bonds. In particular, this work discloses the dual role of organotrifluoroborates serving both as a coupling partner and an electrolyte in C(sp³)–H functionalization.

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Article information

DOI: https://doi.org/10.1039/D2GC02204D
Article type: Communication
Submitted: 10 Jun 2022
Accepted: 12 Sep 2022
First published: 12 Sep 2022

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Green Chem., 2022,24, 7883-7888

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Catalyst-free benzylic C(sp³)–H cross-coupling with organotrifluoroborates enabled by electrochemistry

C. Li, R. Ding, H. Guo, S. Xia, L. Shu, P. Wang and H. Li, Green Chem., 2022, 24, 7883 DOI: 10.1039/D2GC02204D

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