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Iodine‐Promoted Sequential C( sp 3 )H Functionalization Reactions: An Annulation Strategy for the Construction of 3‐Methylthio‐4‐arylmaleimides
Author(s) -
Gao Qinghe,
Wu Xia,
Li Yuhong,
Liu Shan,
Meng Xianggao,
Wu Anxin
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400474
Subject(s) - annulation , chemistry , reagent , iodine , surface modification , combinatorial chemistry , pyrrole , aryl , medicinal chemistry , organic chemistry , catalysis , alkyl
A new process has been developed for the iodine‐promoted sequential C( sp 3 )H bond functionalization of methyl ketones and acetamides. This reaction represents a novel annulation strategy for the synthesis of 3‐(methylthio)‐4‐aryl‐1 H ‐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.