Issue 72, 2016
From the journal:

Chemical Communications

Lewis acid catalysis: catalytic hydroboration of alkynes initiated by Piers' borane†

Mirco Fleige,‡a   Juri Möbus,‡a   Thorsten vom Stein,a   Frank Gloriusa  and  Douglas W. Stephan*a  

* Corresponding authors

a Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6, Canada
E-mail: dstephan@chem.utoronto.ca

Abstract

Terminal and internal alkynes are efficiently hydroborated to (E)-alkenyl pinacol boronic esters with excellent yields and selectivities using a Lewis acid catalyst. In the case of Piers' borane (HB(C6F5)2) the borane acts as a pre-catalyst generating dissymmetrically gem-diborylated species of the form RCH2CR′(Bpin)(B(C6F5)2) which are the active catalysts.

Graphical abstract: Lewis acid catalysis: catalytic hydroboration of alkynes initiated by Piers' borane

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Article information

DOI
https://doi.org/10.1039/C6CC05360B
Article type
Communication
Submitted
28 Jun 2016
Accepted
12 Jul 2016
First published
12 Jul 2016

Chem. Commun., 2016,52, 10830-10833

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Lewis acid catalysis: catalytic hydroboration of alkynes initiated by Piers' borane

M. Fleige, J. Möbus, T. vom Stein, F. Glorius and D. W. Stephan, Chem. Commun., 2016, 52, 10830 DOI: 10.1039/C6CC05360B

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