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

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Abstract

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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Nickel-Catalyzed Carboxylation of Aryl and Vinyl Chlorides Employing Carbon Dioxide

T. Fujihara, K. Nogi, T. Xu, J. Terao, Y. Tsuji, J. Am. Chem. Soc., 2012, 134, 9106-9109.

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Key Words

carboxylation of arenes, manganese

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ID: J42-Y2015