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Direct Photocatalytic Synthesis of Medium‐Sized Lactams by C−C Bond Cleavage
Author(s) -
Wang Na,
Gu QiangShuai,
Li ZhongLiang,
Li Zhuang,
Guo YuLong,
Guo Zhen,
Liu XinYuan
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808890
Subject(s) - aryl , functional group , combinatorial chemistry , substrate (aquarium) , bond cleavage , photocatalysis , ring (chemistry) , chemistry , cleavage (geology) , scope (computer science) , reaction conditions , catalysis , organic chemistry , materials science , computer science , composite material , oceanography , alkyl , fracture (geology) , geology , polymer , programming language
Reported is a novel two‐step ring‐expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones. This step‐economic approach features a remote radical (hetero)aryl migration from C to N under visible‐light conditions. Broad substrate scope, good functional‐group tolerance, high efficiency, and mild reaction conditions make this procedure very attractive. In addition, this method also provides expedient access to 13–15‐membered macrolactams upon an additional one‐step manipulation. Mechanistic studies indicate that the reaction involves an amidyl radical and is promoted by acid.