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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 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.