期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 46, 页码 19268-19274出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c09445
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资金
- Cambridge Display Technologies/Sumitomo
- EPSRC Centre for Doctoral Training-Syn Tech [EPS024220/1]
- Royal Society
- EPSRC [EP/S020292/1]
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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