Light-promoted photocatalyst-free and redox-neutral hydrosulfonylation of unactivated alkenes using sulfinic acid

作者全名：Song, Yibo; Li, Cheng; Hu, Xueyuan; Zhang, Hongdie; Mao, Yujian; Wang, Xiachang; Wang, Chen; Hu, Lihong; Yan, Jianming

作者地址：[Song, Yibo; Hu, Xueyuan; Yan, Jianming] Chongqing Med Univ, Coll Pharm, Chongqing 400016, Peoples R China; [Li, Cheng; Zhang, Hongdie; Mao, Yujian; Wang, Xiachang; Hu, Lihong; Yan, Jianming] Nanjing Univ Chinese Med, Sch Pharm, Nanjing 210023, Peoples R China; [Wang, Chen] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China

通信作者：Hu, XY; Yan, JM (通讯作者)，Chongqing Med Univ, Coll Pharm, Chongqing 400016, Peoples R China.; Hu, LH; Yan, JM (通讯作者)，Nanjing Univ Chinese Med, Sch Pharm, Nanjing 210023, Peoples R China.

来源：GREEN CHEMISTRY

ESI学科分类：CHEMISTRY

WOS号：WOS:001216693000001

JCR分区：Q1

影响因子：9.3

年份：2024

卷号：26

期号：11

开始页：6578

结束页：6583

文献类型：Article

关键词：　

摘要：A hydrosulfonylation reaction of unactivated alkenes with sulfinic acids was realized under light irradiation. This reaction features photocatalyst- and additive-free conditions. A diverse set of unactivated alkenes can be transformed into alkyl-substituted sulfones with good yields and anti-Markovnikov regioselectivity. The present protocol was amenable to gram-scale synthesis, as well as late-stage modification of drugs and natural products. Preliminary mechanistic studies on UV-visible light absorption suggested the key role of sulfinic acid as a light-absorbing species. DFT calculations also shed light on the mechanism of this reaction, which may involve a radical chain pathway. Using sulfinic acid as a sulfonyl source, we have developed a light-promoted photocatalyst-free alkene hydrosulfonylation reaction without any additives.

基金机构：Natural Science Foundation of Jiangsu Province [BK20230442]; Natural Science Foundation of Jiangsu Province, China [013074004035]; Jiangsu Specially Appointed Professor Plan [013074004035P]; Nanjing University of Chinese Medicine [172020320220090 W0072]; CQMU Program for Youth Innovation in Future Medicine

基金资助正文：Financial support from the Natural Science Foundation of Jiangsu Province, China (BK20230442 to J. Y.), the Jiangsu Specially Appointed Professor Plan (013074004035 to J.Y.), the Nanjing University of Chinese Medicine (013074004035P to J. Y.) and the CQMU Program for Youth Innovation in Future Medicine (172020320220090 W0072) is greatly appreciated. We thank Prof. Zhong-Quan Liu at the Nanjing University of Chinese Medicine for helpful discussion.