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Org Lett. 2015 Nov 6;17(21):5276-9. doi: 10.1021/acs.orglett.5b02645. Epub 2015 Oct 9.

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

Author information

1
Faculty of Pharmaceutical Sciences, Hokkaido University , Sapporo 060-0812, Japan.
2
ACT-C, Japan Science and Technology Agency (JST), Sapporo 060-0812, Japan.

Abstract

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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