Categories: C-B Bond Formation > Synthesis of potassium trifluoroborates >
Synthesis of aryltrifluoroborates
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A nickel-catalyzed Miyaura borylation of aryl and heteroaryl halides and
pseudohalides using tetrahydroxydiboron (BBA) proved to be widely functional
group tolerant and applicable to the synthesis of a broad range of aryltrifluoroborates
at room temperature.
A. Molander, L. N. Cavalcanti, C. García-García, J. Org. Chem., 2013,
78, 6427-6439.
A simple transition-metal-free borylation reaction of aryl bromides with
bis-boronic acid (BBA) provides arylboronic acids at mild temperatures directly
without any deprotection steps and purified by conversion to trifluoroborate
salts. The functional group tolerance was considerably high.
T. Lim, J. Y. Ryoo, M. S. Han, J. Org. Chem., 2020, 85,
10966-10972.
A simple and efficient palladium-catalyzed reaction of aryl chlorides with
tetrahydroxydiboron gives arylboronic acids. To ensure preservation of the
carbon-boron bond, the boronic acids were efficiently converted in situ to
trifluoroborate derivatives or boronates in very good yields. Finally, a
two-step, one-pot method for the synthesis of biaryls from two aryl chlorides
was developed.
G. A. Molander, S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc., 2010,
132, 17701-17703.
Arylboronic acids and aryl trifluoroborates are synthesized in a one-pot
sequence by Ir-catalyzed borylation of arenes. To prepare the arylboronic acids,
the Ir-catalyzed borylation is followed by oxidative cleavage of the pinacol
boronates with NaIO4. To prepare the aryltrifluoroborate, the
Ir-catalyzed borylation is followed by displacement of pinacol by KHF2.
J. M. Murphy, C. C. Tzschucke, J. F. Hartwig, Org. Lett., 2007,
9, 757-760.