Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions

Bincy Chindan, Anagha Syam, Hariharan Mahendran and Ramesh Rasappan*

*School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Vithura, Thiruvananthapuram, Kerala 695551, India, Email: rriisertvm.ac.in

B. Chindan, A. Syam, H. Mahendran, R. Rasappan, Org. Lett., 2023, 25, 7751-7756.

DOI: 10.1021/acs.orglett.3c03206

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Abstract

Hydrosilylation of alkynes inevitably yields α- and β-isomers of vinyltrialkoxysilanes. A cross-electrophile C(sp²)-C(sp²) coupling of bromoalkenes yields exclusively α-vinyltrialkoxysilanes with good functional group compatibility under mild reaction conditions.

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proposed mechanism

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Key Words

vinylsiloxanes, alkenylation, manganese

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ID: J54-Y2023