Synthesis of Allylsilanes via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Allyl Alcohols

Bo Yang and Zhong-Xia Wang*

*CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People’s Republic of China, Email: zxwangustc.edu.cn

B. Yang, Z.-X. Wang, Org. Lett., 2019, 21, 7965-7969.

DOI: 10.1021/acs.orglett.9b02946

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Abstract

A NiCl₂(PMe₃)₂-catalyzed reaction of allyl alcohols with silylzinc reagents, including PhMe₂SiZnCl, Ph₂MeSiZnCl, and Ph₃SiZnCl, provides allylsilanes in high yields. The reaction exhibited high regioselectivity and E/Z-selectivity when 1- or 3-aryl-substituted allyl alcohols were used as the substrates.

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Key Words

allylsilanes

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ID: J54-Y2019