Thiol-Mediated α-Amino Radical Formation via Visible-Light-Activated Ion-Pair Charge-Transfer Complexes
Smith, Milo A
Gaunt, Matthew J
Journal of the American Chemical Society
American Chemical Society
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Kohara, K., Trowbridge, A., Smith, M. A., & Gaunt, M. J. (2021). Thiol-Mediated α-Amino Radical Formation via Visible-Light-Activated Ion-Pair Charge-Transfer Complexes. Journal of the American Chemical Society, (jacs.1c09445) https://doi.org/10.1021/jacs.1c09445
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.
Cambridge Display Technologies / Sumitomo: for PhD studentship to K.K; EPSRC Centre for Doctoral Training – SynTech EPS024220/1 to MAS; Royal Society: for Wolfson Merit Award to M.J.G; EPSRC: for EP/S020292/1.
Engineering and Physical Sciences Research Council (EP/S020292/1)
Engineering and Physical Sciences Research Council (EP/S024220/1)
Engineering and Physical Sciences Research Council (2276993)
External DOI: https://doi.org/10.1021/jacs.1c09445
This record's URL: https://www.repository.cam.ac.uk/handle/1810/330684
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