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Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes

Trevor W. Butcher, Edward J. McClain, Tyler G. Hamilton, Trina M. Perrone, Kayla M. Kroner, Gregory C. Donohoe, Novruz G. Akhmedov, Jeffrey L. Petersen and Brian V. Popp*

*C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States, Email: Brian.Poppmail.wvu.edu

T. W. Butcher, E. J. McClain, T. G. Hamilton, T. M. Perrone, K. M. Kroner, G. C. Donohoe, N. G Akhmedov, J. L. Petersen, B. V. Popp, Org. Lett., 2016, 18, 6428-6431.

DOI: 10.1021/acs.orglett.6b03326 (free Supporting Information)



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Abstract

Regioselective copper-catalyzed boracarboxylation of vinyl arenes with bis(pinacolato)diboron and carbon dioxide provides boron-functionalized α-aryl carboxylic acids in good 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.

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Key Words

carboxylation, borylation


ID: J54-Y2016