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Technology Spotlights

Potassium Organotrifluoroborates

Organotrifluoroborates: Versatile and Stable Boronic Acid Surrogates

Prof. Gary Molander has extensively developed the chemistry of organotrifluoroborates. These bench stable boronic acid surrogates are useful for Suzuki-Miyaura cross-coupling reactions and have also been used for a variety of other C-C bond forming reactions. Importantly, these reagents are compatible with a wide range of functional groups and are stable to many commonly used and harsh reaction conditions.


Benefits of Organtrifluoroborates:
  • Bench stable reagents that can be stored indefinitely
  • Can be effectively coupled with a wide range of organic electrophiles
  • Exist as tetracoordinated monomeric species
  • Are less prone to protodeboronation than their boronic acid or boronate ester counterparts

Suzuki-Miyaura Cross-Coupling with Organotrifluoroborates


 


The Versatility of Organotrifluoroborates


Organotrifluoroborates from Aldrich


Product # Description Molecular Formula
684961 Potassium 2-furantrifluoroborate
711101 Potassium pyridine-3-trifluoroborate
711144 Potassium 1H-pyrazole-3-trifluoroborate
681342 Potassium (bromomethyl)trifluoroborate
718947 Potassium (iodomethyl)trifluoroborate
655228 Potassium vinyltrifluoroborate
730432 Potassium propynyltrifluoroborate
659274 Potassium allyltrifluoroborate
662984 Potassium cyclopropyltrifluoroborate
711098 Potassium pyrimidine-5-trifluoroborate
723797 Potassium thiophene-2-trifluoroborate
667145 Potassium sec-butyltrifluoroborate
728799 Potassium 2-bromopyridine-3-trifluoroborate
717517 Potassium 6-bromopyridine-3-trifluoroborate
728802 Potassium 2-chloropyridine-3-trifluoroborate
723568 Potassium pyridine-4-trifluoroborate
666017 Potassium cyclopentyltrifluoroborate
710075 (Thiomorpholinium-4-ylmethyl)trifluoroborate - internal salt
706116 Potassium benzofurazan-5-trifluoroborate
723592 Potassium (2-nitrophenyl)trifluoroborate
719013 (Piperidinium-1-ylmethyl)trifluoroborate - internal salt
710083 [(4-methylpiperazin-1-ium-1-yl)methyl]trifluoroborate - internal salt
723991 Potassium 2-fluoro-5-formylphenyltrifluoroborate
659789 Potassium 3-carboxyphenyltrifluoroborate
563056 Potassium benzyltrifluoroborate
710881 Potassium phenoxymethyltrifluoroborate

 

For a complete list of organotrifluoroborates from Aldrich, visit Aldrich.com/tfb.

References:

  1.  Molander, G. A.; Figueroa, R. Aldrichimica Acta . 2005, 38, 49-56.
  2.  Genêt, J.-P.; Darses, S. Eur. J. Org. Chem. 2003, 4313-4327.