Research Progress in C—S Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions

doi:10.6023/cjoc202006064

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 171-184.DOI: 10.6023/cjoc202006064 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑

REVIEWS

非光催化与电化学体系下有机硫试剂参与的烯烃构建C—S键研究进展

王柏文^a^,^b, 周永军^a, 罗时荷^a^,^b^,^*(), 罗晓燕^a, 陈伟清^a, 杨诗敏^a, 汪朝阳^a^,^b^,^*()

a 华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医药分析化学重点实验室广州 510006
b 华南理工大学广东省功能分子工程重点实验室广州 510640

收稿日期:2020-06-29 修回日期:2020-07-24 发布日期:2020-08-11
通讯作者: 罗时荷, 汪朝阳
作者简介:
* Corresponding authors. E-mail: wangzy@scnu.edu.cn; pinky.r@163.com
基金资助:
广州市科技计划科学研究专项(201607010251); 广东省科技计划(2017A010103016); 广东省功能分子工程重点实验室开放课题(2017kf01)

Research Progress in C—S Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions

Bowen Wang^a^,^b, Yongjun Zhou^a, Shihe Luo^a^,^b^,^*(), Xiaoyan Luo^a, Weiqing Chen^a, Shimin Yang^a, Zhaoyang Wang^a^,^b^,^*()

a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
b Key Lab of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640

Received:2020-06-29 Revised:2020-07-24 Published:2020-08-11
Contact: Shihe Luo, Zhaoyang Wang
Supported by:
the Science and Technology Project Scientific Special of Guangzhou City(201607010251); the Guangdong Provincial Science and Technology Project(2017A010103016); the Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province(2017kf01)

Olefin is an important synthetic synthon, and its concise and efficient transformation has been a research hotspot in the field of organic synthesis. In recent years, the C—S bond formation based on the olefin skeleton has received particular attention from scientists. Alkenes can react with common organic sulfur-containing reagents, including thiol, disulfide, sulfoxide, sulfonyl hydrazide, sulfonyl chloride, sodium sulfinate and other kinds of organosulfur reagents to build C—S bonds at the α-position or β-position of olefin to synthesize sulfide, sulfoxide or sulfone. Thus, according to the different classification of the used organosulfur reagents, the recent research progresses in C—S bond formation reaction of olefins with organic sulfur reagents under photocatalyst-free conditions and non-electrochemical method is summarized. In the future, among the researches on the C—S bond formation reactions of olefins with inexpensive organosulfur reagents, asymmetrical synthesis and various difunctionalizations are still promising directions.

Key words: alkene, C—S bond formation reaction, thiol, sodium sulfinate, aryl ethylene, thioetherification, difunctionalization

Cite this article

Bowen Wang, Yongjun Zhou, Shihe Luo, Xiaoyan Luo, Weiqing Chen, Shimin Yang, Zhaoyang Wang. Research Progress in C—S Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 171-184.

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Fig. & Tab. 10

Scheme 1. Thioetherification reactions between arylthiols and aryl alkenes under different conditions

Scheme 2. Reaction mechanism for acetamidosulfenylation of alkenes with nitriles and thiols

Scheme 3. Thioetherification reactions between thiols andα,β-unsaturated ketones under different conditions

Scheme 4. Metal-catalyzed thioetherification of thiols and heteroatom-containing olefins

Scheme 5. Proposed mechanism of 3,4-anti-Markovnikov hydrothiolation of 1,3-dienes

Scheme 6. Direct thioetherification of 1,1-diarylethene

Scheme 7. Oxysulfonylation of alkenyl oximes with sodium sulfinates

Scheme 8. Synthesis ofα-arylhydrazo-β-ketosulfones

Scheme 9. Selenide-catalyzed azidothiolation ofN-allyl sulfonamides

. Figure 1 Some electrophilic organosulfur reagents

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非光催化与电化学体系下有机硫试剂参与的烯烃构建C—S键研究进展

Research Progress in C—S Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions

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