Formation of Carbanions from Carboxylate Ions Bearing Electron-Withdrawing Groups via Photoinduced Decarboxylation: Addition of Generated Carbanions to Benzaldehyde

Abstract

The photoinduced decarboxylation of carboxylate ions bearing electron-withdrawing groups using biphenyl and 1,4-dicyanonaphthalene leads to the efficient generation of carbanions under mild conditions. The efficiency of the carbanion generation is strongly dependent on the single-electron transfer from the photogenerated radical anion of the electron-acceptor to the radical. In particular, the cyanomethyl anion formed using this photochemical method can be added to benzaldehydes to give the corresponding adducts.