Issue 2, 2014

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
10 10 2013
Accepted
08 11 2013
First published
08 11 2013

Chem. Sci., 2014,5, 694-698

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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