Design, generation, and synthetic application of borylzincate: borylation of aryl halides and borylzincation of benzynes/terminal alkyne

J Am Chem Soc. 2013 Dec 18;135(50):18730-3. doi: 10.1021/ja409748m. Epub 2013 Dec 10.

Abstract

Borylzincate was generated in situ from dialkylzinc, diboron, and metal alkoxide. Model DFT calculations showed that although the formation of borylzincate is kinetically favorable, it is thermodynamically unfavorable. Therefore, we designed a successive reaction sequence that would provide a compensating energy gain. This enabled Zn-catalyzed borylation of aryl halides and borylzincation of benzynes and terminal alkyne from diborons without the need for any cocatalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Benzene Derivatives / chemistry*
  • Boron Compounds / chemistry*
  • Halogens / chemistry*
  • Kinetics

Substances

  • Alkynes
  • Benzene Derivatives
  • Boron Compounds
  • Halogens
  • benzyne