Photocatalysis and Light-Induced Electron Transfer Reactions of Tertiary Amines

Abstract

Photoinduced electron transfer is discussed between various excited acceptors and tertiary alkylamines of various structure. The reactions between indigoid dyes (thioindigo, N,N'-diacetylindigo and oxalylindigo) with triethylamine are described. The amine is readily oxidized to a radical cation which, in turn, is easily deprotonated to give a electron donating free radical. A sequence of electron-proton-electron loss as net hydride donation can take place with acceptors set up to undergo complimentary processes, the latter include both thioindigo and N,N'-diacetylindigo. The substituted tertiary amines were photooxidized with various acceptors to give radical cations which could undergo C-C bond cleavage in competition with deprotonation. The significance and possible applications of these reactions are discussed. [on SciFinder (R)]