Iodine-Promoted Sequential C(sp3)H Functionalization Reactions: An Annulation Strategy for the Construction of 3-Methylthio-4-arylmaleimides

A new process has been developed for the iodine‐promoted sequential C(sp3)H bond functionalization of methyl ketones and acetamides. This reaction represents a novel annulation strategy for the synthesis of 3‐(methylthio)‐4‐aryl‐1H‐pyrrole‐2,5‐diones, and involves an α‐ketoimide as the key intermed...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2014-10, Vol.356 (14-15), p.2924-2930
Main Authors: Gao, Qinghe, Wu, Xia, Li, Yuhong, Liu, Shan, Meng, Xianggao, Wu, Anxin
Format: Article
Language:English
Subjects:
3-methylthio-4-aryl-1H-pyrrole-2
3‐methylthio‐4‐aryl‐1H‐pyrrole‐2,5‐diones
5-diones
Bearing
Bonding
C(sp3)H functionalization
Chemical reactions
Functional groups
iodine-promoted reaction
Ketones
methylthiolation
Organic chemistry
Strategy
Synthesis
α-ketoimides
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Summary:A new process has been developed for the iodine‐promoted sequential C(sp3)H bond functionalization of methyl ketones and acetamides. This reaction represents a novel annulation strategy for the synthesis of 3‐(methylthio)‐4‐aryl‐1H‐pyrrole‐2,5‐diones, and involves an α‐ketoimide as the key intermediate. Furthermore, DMSO was converted to DMS in situ, which served as the methylthiolation reagent in the reaction. This protocol constitutes an efficient and convenient method for the methylthiolation of substrates bearing a wide range of functional groups.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400474