Regioselective Copper-Catalyzed Carboxylation of Allylboronates with Carbon Dioxide
Hung A. Duong*, Paul B. Huleatt, Qian-Wen Tan and Eileen Lau Shuying
*Organic Chemistry, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros #07-01, Singapore 138665, Email: duong_hungices.a-star.edu.sg
H. A. Duong, P. B. Huleatt, Q.-W. Tan, E. L. Shuying, Org. Lett., 2013, 15, 4034-4037.
In the presence of a Cu(I)/NHC catalyst, highly regioselective reactions of allylboronic pinacol esters with CO2 (1 atm) give exclusively the more substituted β,γ-unsaturated carboxylic acids in most cases. Various substituted carboxylic acids can be prepared via this method, including compounds featuring all-carbon quaternary centers.
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