Selectfluor-Promoted Reactions of Aryl Methyl Ketones with Dimethyl Sulfoxide to Give 2,5-Diacylthiophenes and β-Acyl Allylic Methylsulfones
Hao Lü, Jiayi Chen, Wenjun Zhou, Lifen Peng, Shuang‐Feng Yin, Nobuaki Kambe, Renhua Qiu
Abstract
In this paper, a convenient synthesis of 2,5-diacylthiophenes and β-acyl allylic methylsulfones from aryl methyl ketones with dimethyl sulfoxide (DMSO) through Selectfluor-promoted cascade cyclization and cross-coupling reactions by simple solvent modification is described. This method enables the formation of new C-C and C-S bonds via the selection of different solvent ratios, in which DMSO molecules as synthons can be selectively introduced into methyl ketones. The features of this transformation include readily available starting materials, excellent chemoselectivity, and good functional group tolerance.
Topics & Concepts
ChemistryAllylic rearrangementChemoselectivitySelectfluorDimethyl sulfoxideArylSolventSynthonOrganic chemistryHalogenationCombinatorial chemistryReagentAlkylCatalysisSulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsChemical Synthesis and Reactions