Cobalt- and Nickel-Catalyzed Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates Utilizing CO2
Keisuke Nogi, Tetsuaki Fujihara*, Jun Terao and Yasushi Tsuji*
*Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan, Email: tfujiscl.kyoto-u.ac.jp, ytsujiscl.kyoto-u.ac.jp
K. Nogi, T. Fujihara, J. Terao, Y. Tsuji, J. Org. Chem., 2015, 80, 11618-11623.
DOI: 10.1021/acs.joc.5b02307 (free Supporting Information)
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A highly efficient cobalt-catalyzed reductive carboxylation reaction of alkenyl trifluoromethanesulfonates (triflates) enables the synthesis of α,β-unsaturated carboxylic acids in the presence of Mn powder as a reducing reagent under 1 atm pressure of CO2 at room temperature. Moreover, the carboxylation of sterically hindered aryl triflates proceeds smoothly in the presence of a nickel or cobalt catalyst.
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T. Fujihara, K. Nogi, T. Xu, J. Terao, Y. Tsuji, J. Am. Chem. Soc., 2012, 134, 9106-9109.