Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

文献信息

发布日期 2019-11-06

DOI 10.1039/C9QO01274E

影响因子 5.281

作者

Shengqing Ye, Kaida Zhou, Pornchai Rojsitthisak

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摘要

Metal-free insertion of sulfur dioxide with aryl iodides and silyl enolates or allylic bromide under ultraviolet irradiation at room temperature is accomplished. This protocol provides a convenient route to sulfonated cyclic compounds under mild conditions. Not only N-(2-iodophenyl)-N-methylmethacrylamides but also 1-iodo-2-allenoxybenzene is workable. A plausible mechanism is proposed, which shows that during the reaction process, aryl radicals formed in situ from aryl iodides under ultraviolet irradiation undergo intramolecular 5-exo-cyclization, with subsequent sulfonylation via insertion of sulfur dioxide. The resulting sulfonyl radicals are further trapped by silyl enolates or allylic bromide giving rise to sulfonated cyclic compounds.

期刊推荐

Russian Journal of Bioorganic Chemistry

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Current Opinion in Colloid & Interface Science

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

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

Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

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来源期刊

Organic Chemistry Frontiers

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