Ligand-Controlled Regiodivergent Copper-Catalyzed Alkylboration of Alkenes

Angew Chem Int Ed Engl. 2015 Oct 26;54(44):12957-61. doi: 10.1002/anie.201506713. Epub 2015 Sep 4.

Abstract

A novel copper-catalyzed regiodivergent alkylboration of alkenes with bis(pinacolato)diboron and alkyl halides has been developed. The regioselectivity of the alkylboration was controlled by subtle differences in the ligand structure. The reaction thus enables the practical, regiodivergent synthesis of two different alkyl boronic esters with complex structures from a single alkene.

Keywords: copper; cross-coupling; difunctionalization; homogeneous catalysis; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Catalysis
  • Copper / chemistry*
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Boron Compounds
  • Ligands
  • Organometallic Compounds
  • Copper