Borane-Catalysed Hydroboration of Alkynes and Alkenes

Nate W. J. Ang, Cornelia S. Buettner, Scott Docherty, Alessandro Bismuto, Jonathan R. Carney, Jamie H. Docherty, Michael J. Cowley, Stephen P. Thomas*

*EaStCHEM School of Chemistry, Joseph Black Building, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ, UK, Email: Stephen.Thomased.ac.uk

N. W. J. Ang, C. S. Buettner, S. Docherty, A. Bismuto, J. R. Carney, J. H. Docherty, M. J. Cowley, S. P. Thomas, Synthesis, 2018, 50, 803-808.

DOI: 10.1055/s-0036-1591719

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Abstract

Simple, commercially available borane adducts, H₃B·THF and H₃B·SMe₂ catalyse a highly regioselective hydroboration of terminal alkynes and alkenes with pinacolborane to give linear boronic esters. The reaction tolerates ester, amine, ether and halide substituents. This catalytic process shows comparable reactivity to transition-metal-catalysed hydroboration protocols.

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Key Words

borane, hydroboration, akenylboronates, alkylboronates, alkynes, alkenes, main-group, catalysis

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ID: J66-Y2018