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Gold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones
The Journal of Organic Chemistry ( IF 3.3 ) 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

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.

中文翻译:


金 (I/III) 催化芳基/乙烯基碘化物磺酰化反应合成芳基砜



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,由配体启用的 Au(I)/Au(III) 氧化还原催化促成。在反应中,芳基亚磺酸钠或磺酸能与芳基/乙烯基碘化物顺利反应,直接构建各种芳基砜。砜合成的强大合成能力体现在其易于获得和处理的试剂、良好的官能团兼容性以及复杂生物分子的后期应用。机理研究表明,银盐在与 Au(I)/Au(III) 中间体的金属转移中起着至关重要的作用,金配合物有利于 Au-S 键的形成而不是 Au-O 键的形成。
更新日期:2024-12-17
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