Synthesis of β-hydroxysulfones through a copper(ii)-catalyzed multicomponent reaction with the insertion of sulfur dioxide

Literature Information

Publication Date 2019-05-06
DOI 10.1039/C9QO00520J
Impact Factor 5.281
Authors

Wenlin Xie, Shengqing Ye


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Abstract

A copper(II)-catalyzed aerobic oxidative reaction of arylhydrazines, DABCO·(SO2)2 and alkenes is reported. Diverse β-hydroxysulfones are generated in moderate to good yields through the hydroxysulfonylation of alkenes with the insertion of sulfur dioxide under mild conditions. In some cases, β-ketosulfones are produced, depending on the alkenes utilized. Arylhydrazines serve as the precursors of aryl radicals under aerobic atmosphere, which initiate the reaction. During the reaction process, aryl radicals react with sulfur dioxide leading to arylsulfonyl radicals, which subsequently undergo the hydroxysulfonylation of alkenes with oxygen to provide β-hydroxysulfones and related compounds.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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