通过高价碘（III）羧酸盐的脱羧氟磺酰化反应合成脂肪族磺酰氟

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

作者信息

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

机构信息

School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, China.

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.

出版信息

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

DOI:10.1021/acs.orglett.3c02652

PMID:37656922

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 KHF 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) was realized, as well. Notably, this transformation can be performed under heating conditions without the need for catalysts.

摘要

我们在此公开了一种光催化脱羧氟磺酰化反应，该反应涉及各种高价碘（III）羧酸盐与1,4-二氮杂双环[2.2.2]辛烷-双（二氧化硫）加合物作为磺酰源以及KHF作为理想氟源，通过自由基二氧化硫插入和氟化策略实现。还实现了由PhI（OAc）介导的各种羧酸的一锅光催化脱羧氟磺酰化反应。值得注意的是，这种转化可以在加热条件下进行，无需催化剂。