Aliphatic Sulfonyl Fluoride Synthesis via Decarboxylative Fluorosulfonylation of Hypervalent Iodine(III) Carboxylates

Caiyun Ou; Yinxia Cai; Yuyang Ma; Haozhen Zhang; Xiaoyu Ma; Chao Liu

doi:10.1021/acs.orglett.3c02652

Aliphatic Sulfonyl Fluoride Synthesis via Decarboxylative Fluorosulfonylation of Hypervalent Iodine(III) Carboxylates

Org Lett. 2023 Sep 15;25(36):6751-6756. doi: 10.1021/acs.orglett.3c02652. Epub 2023 Sep 1.

Authors

Caiyun Ou¹, Yinxia Cai¹, Yuyang Ma¹, Haozhen Zhang¹, Xiaoyu Ma¹, Chao Liu^{1

2}

Affiliations

¹ School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, China.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

PMID: 37656922
DOI: 10.1021/acs.orglett.3c02652

Abstract

We disclose herein a photocatalytic decarboxylative fluorosulfonylation reaction of various hypervalent iodine(III) carboxylates in combination with 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a sulfonyl source and KHF₂ as a desirable fluorine source via a radical sulfur dioxide insertion and fluorination strategy. A one-pot photocatalytic decarboxylative fluorosulfonylation reaction of various carboxylic acids mediated by PhI(OAc)₂ was realized, as well. Notably, this transformation can be performed under heating conditions without the need for catalysts.