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Issue 2, 2014
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Iridium-catalyzed diborylation of benzylic C–H bonds directed by a hydrosilyl group: synthesis of 1,1-benzyldiboronate esters

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Abstract

We describe a regioselective diborylation of primary benzylic C–H bonds catalyzed by [Ir(COD)OMe]2 and 4,4′-di-tert-butyl-2,2′-bipyridine (dtbpy). The hydrosilyl group acts as a traceless directing group, providing access to a range of 1,1-benzyldiboronate esters in good yields. Transformations of the 1,1-benzyldiboronate ester products include chemoselective Suzuki–Miyaura cross-couplings and synthesis of tetrasubstituted alkenyl boronate esters.

Graphical abstract: Iridium-catalyzed diborylation of benzylic C–H bonds directed by a hydrosilyl group: synthesis of 1,1-benzyldiboronate esters

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Article information


Submitted
10 Oct 2013
Accepted
08 Nov 2013
First published
08 Nov 2013

Chem. Sci., 2014,5, 694-698
Article type
Edge Article

Iridium-catalyzed diborylation of benzylic C–H bonds directed by a hydrosilyl group: synthesis of 1,1-benzyldiboronate esters

S. H. Cho and J. F. Hartwig, Chem. Sci., 2014, 5, 694
DOI: 10.1039/C3SC52824C

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