Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation.

Abstract

A highly diastereoselective carbon-carbon bond-forming reaction involving the tandem coupling of benzyltriboronates, enoates, and alkyl halides is described. This method was enabled by the discovery of α-diimine nickel catalysts that promote the chemoselective triborylation of benzylic C(sp3)-H bonds using B2Pin2 (Pin = pinacolate). The C-H functionalization method is effective with methylarenes and for the diborylation of secondary benzylic C-H bonds, providing direct access to polyboron building blocks from readily available hydrocarbons. Combination of the benzylic perborylation with a new deborylative conjugate addition-alkylation method enables a one-pot procedure in which multiple simple precursors are combined to generate diastereopure products containing quaternary stereocenters.

DOI: 10.1021/jacs.6b12896

Cite this paper

@article{Palmer2017BenzyltriboronatesBB, title={Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation.}, author={Wystan N. Palmer and Cayetana Zarate and Paul J Chirik}, journal={Journal of the American Chemical Society}, year={2017}, volume={139 7}, pages={2589-2592} }