4.8 Article

NHC-Cu-Catalyzed Protoboration of Monosubstituted Allenes. Ligand-Controlled Site Selectivity, Application to Synthesis and Mechanism

Journal

ORGANIC LETTERS
Volume 15, Issue 6, Pages 1414-1417

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol4004178

Keywords

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Funding

  1. NSF [CHE-1111074]
  2. NIH [GM-47480]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1111074] Funding Source: National Science Foundation

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Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.

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