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Visible‐Light‐Driven Photochemical Activation of sp 3 C−H Bond for Hemiaminal Formation
Author(s) -
Li Lina,
Zhang Guigang,
Savateev Aleksandr,
Kurpil Bogdan,
Antonietti Markus,
Zhao Yubao
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800653
Subject(s) - hemiaminal , iminium , chemistry , photochemistry , nucleophile , yield (engineering) , amide , nucleophilic addition , organic chemistry , ion , catalysis , materials science , metallurgy
Photochemical synthesis of organic chemicals has attracted a massive revitalized research interest. Herein, a metal‐free photochemical system with carbon tetrabromide (CBr 4 ) is developed for the synthesis of hemiaminal compounds. In this reaction system, the sp 3 C−H bond of the N‐alkyl group in the amide is photochemically activated, producing an ionic iminium species. The hemiaminal compounds are produced by nucleophilic attack of the iminium ion by alcohol in the presence of base. This photochemical conversion system shows high yield and broad substrate scope.