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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:,

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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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

Key Words

cyclopentanes, diphenylsilane

ID: J54-Y2018