Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation

W. Neil Palmer, Cayetana Zarate, Paul J. Chirik

Research output: Contribution to journalArticle

54 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2589-2592
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number7
DOIs
StatePublished - Feb 22 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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