Dienylation of N-benzoylhydrazones with CF3-substituted homoallenylboronates in water

Wei-Wei Ma; Chao Yang; Qiang Xie; Yun-He Xu

doi:10.1039/D1OB02335G

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Dienylation of N-benzoylhydrazones with CF₃-substituted homoallenylboronates in water†

Wei-Wei Ma,^a Chao Yang,

^a Qiang Xie*^c and Yun-He Xu

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R China
E-mail: xyh0709@ustc.edu.cn

^b State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R China

^c Department of Nuclear Medicine the First Affiliated Hospital of USTC; the Division of Life Sciences and Medicine, University of Science and Technology of China, Hefei, Anhui 230001, P. R China
E-mail: xieqiang1980@ustc.edu.cn

Abstract

A convenient method for the dienylation of N-benzoylhydrazones in water has been developed. This protocol expanded the synthetic application of functionalized homoallenylboronates to provide the useful 2-aminomethyl-1,3-diene derivatives with high efficiency (up to 99% yield) and stereoselectivity without using any catalyst, additive or inert atmosphere. Furthermore, the transformation of a 2-aminomethyl-1,3-diene derivative to synthesize a functionalized pyrrolidine derivative was also explored.

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Article information

DOI: https://doi.org/10.1039/D1OB02335G
Article type: Communication
Submitted: 29 Nov 2021
Accepted: 14 Jan 2022
First published: 14 Jan 2022

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Org. Biomol. Chem., 2022,20, 1386-1390

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Dienylation of N-benzoylhydrazones with CF₃-substituted homoallenylboronates in water

W. Ma, C. Yang, Q. Xie and Y. Xu, Org. Biomol. Chem., 2022, 20, 1386 DOI: 10.1039/D1OB02335G

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Organic & Biomolecular Chemistry