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

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posted on 2015-11-06, 00:00 authored by Tsuyoshi Mita, Kenta Suga, Kaori Sato, Yoshihiro Sato
By using a strained four-membered ring disilane (3,4-benzo-1,1,2,2-tetra­ethyldisila­cyclobutene) and CsF, a wide range of aryl, alkenyl, alkynyl, benzyl, allyl, and alkyl halides was successfully carboxylated under an ambient CO2 atmosphere (CO2 balloon) at room temperature within 2 h. In this carboxylation, a highly reactive silyl anion, which is generated from the disilane and CsF, is a key to facilitating the formation of a carbanion equivalent. The resulting anionic species can be trapped with CO2 to produce carboxylic acids with high efficiency.

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