One-Pot Synthesis of Arylboronic Acids and Aryl Trifluoroborates by Ir-Catalyzed Borylation of Arenes
Jaclyn M. Murphy, Carl Christoph Tzschucke, John F. Hartwig
Abstract
Jaclyn M. Murphy, Carl Christoph Tzschucke, John F. Hartwig
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.
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[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.
Key concepts: Borylation, Pinacol, Chemistry, Aryl, Catalysis, Combinatorial chemistry, Organic chemistry, Alkyl