Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Yunfei Sha; Jiandong Liu; Liang Wang; Demin Liang; Da Wu; Hegui Gong

doi:10.1039/D1OB00791B

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Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides†

Yunfei Sha,^a Jiandong Liu,^b Liang Wang,^a Demin Liang,^a Da Wu*^a and Hegui Gong

*^b

Author affiliations

* Corresponding authors

^a Technical Center, Shanghai Tobacco Group Corporation Ltd, 3733 Xiu-Pu Road, Shanghai 201315, China
E-mail: wud@sh.tobacco.com.cn

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

Abstract

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB00791B
Article type: Communication
Submitted: 23 Apr 2021
Accepted: 18 May 2021
First published: 18 May 2021

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Org. Biomol. Chem., 2021,19, 4887-4890

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Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Y. Sha, J. Liu, L. Wang, D. Liang, D. Wu and H. Gong, Org. Biomol. Chem., 2021, 19, 4887 DOI: 10.1039/D1OB00791B

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Organic & Biomolecular Chemistry

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides†

Abstract

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Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

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