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Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes

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posted on 30.11.2016, 00:00 by Trevor W. Butcher, Edward J. McClain, Tyler G. Hamilton, Trina M. Perrone, Kayla M. Kroner, Gregory C. Donohoe, Novruz G. Akhmedov, Jeffrey L. Petersen, Brian V. Popp
Regioselective copper-catalyzed boracarboxylation of vinyl arenes with bis­(pinacolato)­diboron and carbon dioxide has been achieved. New boron-functionalized α-aryl carboxylic acids, including nonsteroidal anti-inflammatory drugs (NSAIDs), are obtained in moderate to excellent yields. The synthetic utility of the transformation was shown through subsequent derivatization of the carbon–boron bond yielding formal hydroxy- and fluorocarboxylation products as well as anionic difluoroboralactones.