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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 (free Supporting Information)



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Abstract

Simple, commercially available borane adducts, H3BĚTHF and H3BĚSMe2 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


ID: J66-Y2018