Switchable Synthetic Strategy toward Trisubstituted and Tetrasubstituted Exocyclic Alkenes

Sen Zhou, Fangyuan Yuan, Minjie Guo, Guangwei Wang*, Xiangyang Tang, Wentao Zhao*

*Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. China, Email: wanggwtju.edu.cn, wentao_zhaotju.edu.cn

S. Zhou, F. Yuan, M. Guo, G. Wang, X. Tang, W. Zhao, Org. Lett., 2018, 20, 6710-6714.

DOI: 10.1021/acs.orglett.8b02801

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Abstract

Cu(I) catalysis enables an efficient and facile construction of trisubstituted exocyclic alkenes in good yields under mild conditions in the presence of B₂pin₂. Tetrasubsituted borylated or iodinated alkenes can also be isolated depending on the reaction conditions. A preliminary mechanistic study showed that the reaction undergoes a radical process, where B₂pin₂ plays an indispensable role.

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reported methods

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Key Words

cyclopentanes, diphenylsilane

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ID: J54-Y2018