Solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2: synthesis of 2-aminoethyl dithiocarbamates†

Abstract

This study presents a solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS₂, yielding two distinct types of 2-aminoethyl dithiocarbamates without the need for additives or a non-green activation strategy. Featuring excellent atom economy, low-cost starting materials, broad substrate scope, and compatibility with clinically relevant molecules, this reaction is both efficient and sustainable for practical applications. Control experiments and DFT calculations reveal that hydrogen bonding between solvents and aziridines directs selectivity by modulating orbital distributions, clarifying the selective reaction pathways.