Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Nhan N. H. Ton, Binh Khanh Mai*, and Thanh Vinh Nguyen*

*University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States; University of New South Wales, Sydney 2052, NSW, Australia, Email: binh.maipitt.edu, t.v.nguyenunsw.edu.au

N. N. H. Ton, B. K. Mai, T. V. Nguyen, J. Org. Chem., 2021, 86, 9117-9133.

DOI: 10.1021/acs.joc.1c01208

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Abstract

Tropylium salts promote the hydroboration reaction of alkynes to provide a broad range of vinylboronates. Similar metal-free hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction is triggered by the hydride abstraction of pinacolborane with tropylium ion.

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Key Words

vinylboronates, organocatalysis

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ID: J42-Y2021