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Organotrifluoroborate

Class of chemical compounds

Organotrifluoroborates are organoboron compounds that contain an anion with the general formula [RBF3]−. They can be thought of as protected boronic acids, or as adducts of carbanions and boron trifluoride. Organotrifluoroborates are tolerant of air and moisture and are easy to handle and purify. They are often used in organic synthesis as alternatives to boronic acids (RB(OH)2), boronate esters (RB(OR′)2), and organoboranes (R3B), particularly for Suzuki-Miyaura coupling.

Structure

first1 = G.	last1 = Conole	first2 = A.	last2 = Clough	first3 = A.	last3 = Whiting	title = Potassium Trifluorophenylborate	journal = Acta Crystallogr. C	year = 1995	volume = 51	pages = 1056–1059	doi = 10.1107/S0108270194014198	issue = 6	doi-access = }}	space-filling packing diagram of
the crystal structure of K[PhBF3]

Synthesis

Boronic acids RB(OH)2 react with potassium bifluoride K[HF2] to form trifluoroborate salts K[RBF3].

Reactivity

Organotrifluoroborates are strong nucleophiles and react with electrophiles without transition-metal catalysts.

Mechanism

The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully.

References

"Alfa Aesar – Product Flyers & Technical Reviews – Organotrifluoroborates".
(2012-09-09). "Sigma-Aldrich – Chemical Synthesis – Technology Spotlights – Organotrifluoroborates".
(2008). "Potassium Organotrifluoroborates: New Perspectives in Organic Synthesis". [[Chemical Reviews]].
(2007). "Organotrifluoroborates: Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction". [[Accounts of Chemical Research]].
(1995). "Potassium Trifluorophenylborate". [[Acta Crystallographica.
(2012). "Nucleophilicity parameters for designing transition metal-free C–C bond forming reactions of organoboron compounds". [[Chemical Science (journal).
(2010). "Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride". [[Angewandte Chemie.
"Mechanism Of Suzuki-Miyaura Coupling Revealed". [[Chemical & Engineering News]].

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organoboron-compounds anions borates

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