Electrochemical Decarboxylative Silylation of α,β-Unsaturated Carboxylic Acids

An electrochemical method for the decarboxylative silylationof alpha,beta-unsaturated carboxylic acids was developed. A varietyof alkenylsilanes could be obtained in satisfactory yields and excellentselectivities under external oxidant- and metal-free conditions. Mechanisticstudies showed that the formation of the silyl radical was mediatedby NHPI, which produces the hydrogen atom transfer (HAT) reagent phthalimide N-oxyl (PINO) via multiple-site concerted proton-electrontransfer (MS-CPET).

Automated summary

An electrochemical method for the decarboxylative silylation of alpha,beta-unsaturated carboxylic acids has been developed with satisfactory yields and excellent selectivities. Mechanistic studies reveal that NHPI mediates the formation of silyl radicals by generating the HAT reagent PINO via MS-CPET.