Thiol-Mediated α-Amino Radical Formation via Visible-Light-Activated Ion-Pair Charge-Transfer Complexes
Keishi Kohara, Aaron Trowbridge, Milo A. Smith, Matthew J. Gaunt
Abstract
Visible-light-activated electron donor-acceptor complexes offer distinct reaction pathways for the synthesis of complex molecules under mild conditions. Herein, we report a method for the reductive generation of α-amino radicals via the reaction of a visible-light-activated ion-pair charge-transfer complex formed between an in situ-generated alkyl-iminium ion and a thiophenolate. This distinct activation mode is demonstrated through the development of a multicomponent coupling reaction to form substituted aminomethyl-cyclopentanes from secondary amines, cyclopropyl aldehydes, and alkenes. The operationally straightforward transformation displays broad scope and provides a means to generate cyclic amine-containing scaffolds from readily available feedstocks.