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

doi:10.6023/cjoc202006064

有机化学 ›› 2021, Vol. 41 ›› Issue (1): 171-184.DOI: 10.6023/cjoc202006064 上一篇下一篇

所属专题：有机电合成虚拟专辑

综述与进展

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)

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摘要/Abstract

烯烃是重要的合成子, 其简洁高效的合成转化一直是有机合成领域的研究热点. 近年来, 基于烯烃骨架的C—S键成键反应特别受科学家的关注. 烯烃可以与常见的有机含硫试剂(包括硫醇或硫酚、二硫醚、亚砜、磺酰肼、磺酰氯和亚磺酸钠等)反应, 在烯烃的 α-位或者 β-位构筑C—S键来合成硫醚、亚砜或砜类化合物. 鉴于此, 以有机硫试剂的种类为分类依据, 综述了近年来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反应的相关研究. 展望未来, 在烯烃与有机硫试剂的C—S成键反应研究中, 双官能团化反应和不对称催化合成具有较好的应用前景.

关键词: 烯烃, C—S键构建, 硫醇, 亚磺酸钠, 芳基乙烯, 硫醚化反应, 双官能团化反应

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

引用此文

王柏文, 周永军, 罗时荷, 罗晓燕, 陈伟清, 杨诗敏, 汪朝阳. 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[J]. 有机化学, 2021, 41(1): 171-184.

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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图/表 10

图式1. 不同条件下硫酚与芳基乙烯之间的硫醚化反应

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

图式2. 基于烯烃、腈和硫醇反应的酰胺基砜基化反应机理

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

图式3. 不同条件下硫醇与α,β-不饱和酮之间的硫醚化反应

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

图式4. 金属催化硫醇与含杂原子烯烃的硫醚化反应

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

图式5. 1,3-丁二烯的3,4-反马氏硫氢化反应可能的机理

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

图式6. 1,1-二芳基乙烯的直接硫醚化反应

Scheme 6. Direct thioetherification of 1,1-diarylethene

图式7. 烯基肟与亚磺酸钠的氧砜基化反应

Scheme 7. Oxysulfonylation of alkenyl oximes with sodium sulfinates

图式8. α-芳基偶氮基-β-羰基砜的合成

Scheme 8. Synthesis ofα-arylhydrazo-β-ketosulfones

图式9. 硒催化N-烯丙基磺酰胺的叠氮硫醚化反应

Scheme 9. Selenide-catalyzed azidothiolation ofN-allyl sulfonamides

图1. 几种亲电性有机硫试剂

. 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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