Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 7, Pages 2589-2592Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b12896
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Funding
- National Science Foundation [CHE-1265988]
- Eli Lilly Graduate Research Fellowship
- MINECO
- NIH [R01 GM121441]
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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 alpha-diimine nickel catalysts that promote the chemoselective tribor-ylation of benzylic C(sp(3))-H bonds using B(2)Pin(2) (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.
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