Gold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2024-12-17 DOI:10.1021/acs.joc.4c01675
Lizhu Zhang, Wenqian Du, Jiawen Wu, Rongjie Yang, Fen Zhao, Baomin Fan, Zhonghua Xia
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Abstract

A gold-catalyzed sulfonylation of aryl/vinyl iodides to synthesize aryl sulfones facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis was developed. In the reaction, aryl sodium sulfinates or sulphinic acids can react smoothly with aryl/vinyl iodides to directly construct various aryl sulfones. The strong synthetic capabilities of sulfone synthesis are demonstrated by its easily available and handled reagents, good functional group compatibility, and late-stage application of complicated biomolecules. Mechanistic studies suggest that the silver salt plays a crucial role in the transmetalation with the Au(I)/Au(III) intermediate, and the gold complex favors Au–S bond formation over Au–O bond formation.

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金(I/III)催化的芳基/乙烯基碘化物磺酰化反应合成芳基砜
通过配体使能的 Au(I)/Au(III)氧化还原催化,开发了一种金催化的芳基/乙烯基碘化物磺酰化反应,以合成芳基砜。在该反应中,芳基硫酸钠或亚硫酸可与芳基/乙烯基碘化物顺利反应,直接构建各种芳基砜。砜类合成的试剂易得易处理、官能团兼容性好,以及复杂生物大分子的后期应用,都证明了砜类合成的强大合成能力。机理研究表明,银盐在与 Au(I)/Au(III) 中间体的跨金属化过程中起着至关重要的作用,而金配合物则有利于 Au-S 键的形成而非 Au-O 键的形成。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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