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.