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Organotrifluoroborates as Coupling Partners in Suzuki-Miyaura Reactions

By: Josephine Nakhla, Chemfiles Volume 10 Article 3

Suzuki-Miyaura cross-coupling reactions are some of the most common methods for the formation of C–C bonds in organic chemistry. The use of some boronic acids is complicated by their instability and their propensity for trimerization. The advent of boronic acid surrogates such as trifluoroborates has transformed the field, allowing for shelf-storage and usability of otherwise unstable boronic acids. Trifluoroborates exhibit excellent functional group tolerance and stability towards common reagents, which has also lead to their widespread use. Our platform of trifluoroborate salts is continually growing, with new product introductions occurring regularly. Some of our recent additions are listed below.

Benefits of Trifluoroborates:

  • Stable tetracoordinate species
  • Less prone to protodeboronation
  • Prepared from inexpensive KHF2
  • Air and moisture-stable
  • Easily purified via recrystallization, precipitation, or Soxhlet extraction

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References

  1. Molander, G.A.; Ellis, N. Acc. Chem Res. 2007, 40, 275.

For a complete list of Trifluoroborates available from Aldrich Chemistry, please visit aldrich.com/tfb

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