Base and solvent dependency of an oxidative retro-alkylation of secondary and tertiary benzylamines

Abstract

An iodine and caesium carbonate amine oxidation protocol is described. Non-branched secondary benzylamines were cleanly oxidised to aldimines that could be isolated without the need for chromatography. A tertiary amine bearing an ethyl group was oxidatively de-ethylated by iodine and caesium carbonate in a DMSO–water solvent system.