I<sub>2</sub>/DMSO-mediated multicomponent reaction of <i>o</i>-hydroxyaryl methyl ketones, rongalite, and DMSO: access to C3-sulfenylated chromones

Miao Wang(Central China Normal University), Bo‐Cheng Tang(Central China Normal University), Jin‐Tian Ma(Central China Normal University), Zixuan Wang(Central China Normal University), Jia‐Chen Xiang(Central China Normal University), Yan‐Dong Wu(Central China Normal University), Jungang Wang(Guizhou Minzu University), An‐Xin Wu(Central China Normal University)
Organic & Biomolecular Chemistry
January 1, 2019
Cited by 63

Abstract

An efficient I2-DMSO reagent system-mediated multicomponent reaction strategy for the synthesis of C3-sulfenylated chromones from o-hydroxyaryl methyl ketones, rongalite, and dimethyl sulfoxide has been developed. Notably, the double C-S bond cleavages of rongalite and dimethyl sulfoxide served as key steps in this smooth transformation, affording the C1 unit and sulfur source for the assembly of C3-sulfenylated chromones. Preliminary mechanistic studies indicated that in situ generated HCHO and (2-(2-hydroxyphenyl)-2-oxoethyl)dimethylsulfonium iodine were probably the key intermediates in this transformation.


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