One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes

Org Lett. 2007 Mar 1;9(5):757-60. doi: 10.1021/ol062903o. Epub 2007 Feb 3.

Abstract

[reaction: see text] The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.