4.8 Article

Thiol-Mediated α-Amino Radical Formation via Visible-Light-Activated Ion-Pair Charge-Transfer Complexes

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 46, 页码 19268-19274

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AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c09445

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资金

  1. Cambridge Display Technologies/Sumitomo
  2. EPSRC Centre for Doctoral Training-Syn Tech [EPS024220/1]
  3. Royal Society
  4. EPSRC [EP/S020292/1]

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Visible-light-activated electron donor-acceptor complexes provide unique reaction pathways for the synthesis of complex molecules under mild conditions. This study demonstrates a method for the reductive generation of α-amino radicals through the reaction of a visible-light-activated ion-pair charge-transfer complex, allowing for the development of a multicomponent coupling reaction to form substituted aminomethyl-cyclopentanes. The operationally straightforward transformation is versatile and enables the generation of cyclic amine-containing scaffolds from readily available feedstocks.
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 a-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.

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