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

Lizhu Zhang, Wenqian Du, Jiawen Wu, Rongjie Yang, Fen Zhao*, Baomin Fan*, Zhonghua Xia*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)44-51
Number of pages8
JournalJournal of Organic Chemistry
Volume90
Issue number1
DOIs
Publication statusPublished - 10 Jan 2025

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Zhang, L., Du, W., Wu, J., Yang, R., Zhao, F., Fan, B., & Xia, Z. (2025). Gold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones. Journal of Organic Chemistry, 90(1), 44-51. https://doi.org/10.1021/acs.joc.4c01675