Heteroaryl Trifluoroborates for Suzuki-Miyaura Reactions

By: Dr. Josephine Nakhla, Chemfiles Volume 10 Article 2

The cross-coupling of heteroarylboronic acids has been a longstanding challenge, presumably due to the difficulties associated with preparing and isolating heteroarylboronic acids. Molander has recently reported the cross-coupling of heteroaryltrifluoroborates (boronic acid surrogates) with various aryl and heteroaryl halides using a catalyst system comprised of Pd(OAc)2, RuPhos, and Na2CO3 as the base.1,2

Scheme 7: Suzuki coupling of heteroaryl trifluoroborates with heteroaryl and aryl chlorides

Scheme 7: Suzuki coupling of heteroaryl trifluoroborates with heteroaryl and aryl chlorides  (711101 ) (711144)

Benefits of Trifluoroborates:

  • Stable tetracoordinated species
  • Less prone to protodeboronation
  • Prepared from inexpensive KHF2
  • Air and moisture-stable
  • Easily purified

back to top

Materials

     

References

  1. Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973.
  2. Molander, G.A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49.

back to top

Related Links