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A Strained Disilane-Promoted Carboxylation of Organic Halides with CO2 under Transition-Metal-Free Conditions

Tsuyoshi Mita*, Kenta Suga, Kaori Sato and Yoshihiro Sato*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, Email: tmitapharm.hokudai.ac.jp, biyopharm.hokudai.ac.jp

T. Mita, K. Suga, K. Sato, Y. Sato, Org. Lett., 2015, 17, 5276-5279.

DOI: 10.1021/acs.orglett.5b02645 (free Supporting Information)


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Abstract

A highly reactive silyl anion, which is generated from a strained four-membered ring disilane (3,4-benzo-1,1,2,2-tetraethyldisilacyclobutene) and CsF mediates the formation of carbanions from a wide range of aryl, alkenyl, alkynyl, benzyl, allyl, and alkyl halides. The resulting anionic species can be trapped with CO2 to produce carboxylic acids with high efficiency.

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Key Words

carboxylation


ID: J54-Y2015