Ni-catalyzed regioselective hydrobenzylation of alkenes to afford C(sp3)–C(sp3) bonds using BH3 as a reductant

Li Cheng; Quan Lin; Yanhong Song; Hua Chen; Hegui Gong; Yunrong Chen

doi:10.1039/D2QO01510B

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Ni-catalyzed regioselective hydrobenzylation of alkenes to afford C(sp³)–C(sp³) bonds using BH₃ as a reductant†

Li Cheng,‡^ab Quan Lin,‡^ab Yanhong Song,^c Hua Chen,^c Hegui Gong

*^b and Yunrong Chen

*^b

Author affiliations

* Corresponding authors

^a School of Materials Science and Engineering, Shanghai University, 99 Shangda Road, Shanghai 200444, China

^b Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, China
E-mail: hegui_gong@shu.edu.cn, yr_chen@shu.edu.cn

^c Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, China

Abstract

The nickel-catalyzed reductive olefin hydrocarbonation reaction is one of the powerful tools for the formation of C(sp³)–C bonds. However, the reductive coupling of alkenes with benzyl halides to afford alkyl–benzyl products has rarely been studied using the well-established Ni/SiH methods. Herein, we report a method of Ni-catalyzed regioselective hydrobenzylation of unactivated alkenes to afford anti-Markovnikov products using BH₃ as a reductant. This method exhibits good functional group tolerance, a wide scope and high regioselectivity. The mild conditions enable the coupling of terminal and internal alkenes with primary and secondary benzyl halides.

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Article information

DOI: https://doi.org/10.1039/D2QO01510B
Article type: Research Article
Submitted: 22 Sep 2022
Accepted: 20 Nov 2022
First published: 22 Nov 2022

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Org. Chem. Front., 2023,10, 369-374

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Ni-catalyzed regioselective hydrobenzylation of alkenes to afford C(sp³)–C(sp³) bonds using BH₃ as a reductant

L. Cheng, Q. Lin, Y. Song, H. Chen, H. Gong and Y. Chen, Org. Chem. Front., 2023, 10, 369 DOI: 10.1039/D2QO01510B

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