Categories: C-B Bond Formation > Synthesis of potassium trifluoroborates >
Synthesis of aryltrifluoroborates
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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.
