Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates

doi:10.6023/cjoc202201046

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2940-2946.DOI: 10.6023/cjoc202201046 Previous Articles Next Articles

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光催化氧化交叉偶联制备对称/不对称硫代磺酸酯

赵健铭, 朱佳顺, 沈佳斌, 张怡岚, 李万梅^*()

杭州师范大学材料与化学化工学院有机硅化学及材料技术教育部重点实验室杭州 311121

收稿日期:2022-01-27 修回日期:2022-04-21 发布日期:2022-05-31
通讯作者: 李万梅
基金资助:
浙江省自然科学基金(LY21B060009); 浙江省“万人计划”(2019R51012)

Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates

Jianming Zhao, Jiashun Zhu, Jiabin Shen, Yilan Zhang, Wanmei Li()

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121

Received:2022-01-27 Revised:2022-04-21 Published:2022-05-31
Contact: Wanmei Li
Supported by:
Natural Science Foundation of Zhejiang Province(LY21B060009); “Ten-Thousand Talents Plan” of Zhejiang Province(2019R51012)

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Abstract

Photocatalysis has become the forefront of international chemical research due to its green and environmentally friendly characteristics. A new protocol to construct S—S(O)₂ bonds using selectfluor as oxidant and eosin Y as photocatalyst under blue light irradiation was reported. This method has advantages of mild conditions, good compatibility of functional groups, and easily preparation of various symmetric or asymmetric thiosulfonates various from the corresponding mercaptans with good conversion rates. Thus, this protocol provides a very valuable reference for developing a catalytic system with mild conditions, high atomic economy and strong universality to achieve efficient and controllable conversion of sulfur-containing organic compounds.

Key words: thiol, photocatalysis, oxidative coupling, thiosulfonate

Cite this article

Jianming Zhao, Jiashun Zhu, Jiabin Shen, Yilan Zhang, Wanmei Li. Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2940-2946.

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Fig. & Tab. 7

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Entry	Catalyst	Oxidant	Solvent	Yield^b/%
1	PC-1	selectfluor	CH₃CN	87
2	PC-2	selectfluor	CH₃CN	50
3	PC-3	selectfluor	CH₃CN	72
4	PC-4	selectfluor	CH₃CN	77
5	PC-5	selectfluor	CH₃CN	64
6	PC-1	CH₃CO₃H	CH₃CN	63
7	PC-1	TBPO	CH₃CN	74
8	PC-1	H₂O₂	CH₃CN	Trace
9	PC-1	selectfluor	H₂O	82
10	PC-1	selectfluor	EtOH	42
11	PC-1	selectfluor	DCM	17
12^c	PC-1	selectfluor	CH₃CN/H₂O	89
13^c	—	selectfluor	CH₃CN/H₂O	Trace
14^c	PC-1	—	CH₃CN/H₂O	34
15^c^,^d	PC-1	selectfluor	CH₃CN/H₂O	64
16^c^,^e	PC-1	selectfluor	CH₃CN/H₂O	90
17^c^,^f	PC-1	selectfluor	CH₃CN/H₂O	78
18^c^,^g	PC-1	selectfluor	CH₃CN/H₂O	92
19^c^,^h	PC-1	selectfluor	CH₃CN/H₂O	58
20^c^,ⁱ	PC-1	selectfluor	CH₃CN/H₂O	78
21^c^,^j	PC-1	selectfluor	CH₃CN/H₂O	77

Entry	Catalyst	Oxidant	Solvent	Yield^b/%
1	PC-1	selectfluor	CH₃CN	87
2	PC-2	selectfluor	CH₃CN	50
3	PC-3	selectfluor	CH₃CN	72
4	PC-4	selectfluor	CH₃CN	77
5	PC-5	selectfluor	CH₃CN	64
6	PC-1	CH₃CO₃H	CH₃CN	63
7	PC-1	TBPO	CH₃CN	74
8	PC-1	H₂O₂	CH₃CN	Trace
9	PC-1	selectfluor	H₂O	82
10	PC-1	selectfluor	EtOH	42
11	PC-1	selectfluor	DCM	17
12^c	PC-1	selectfluor	CH₃CN/H₂O	89
13^c	—	selectfluor	CH₃CN/H₂O	Trace
14^c	PC-1	—	CH₃CN/H₂O	34
15^c^,^d	PC-1	selectfluor	CH₃CN/H₂O	64
16^c^,^e	PC-1	selectfluor	CH₃CN/H₂O	90
17^c^,^f	PC-1	selectfluor	CH₃CN/H₂O	78
18^c^,^g	PC-1	selectfluor	CH₃CN/H₂O	92
19^c^,^h	PC-1	selectfluor	CH₃CN/H₂O	58
20^c^,ⁱ	PC-1	selectfluor	CH₃CN/H₂O	78
21^c^,^j	PC-1	selectfluor	CH₃CN/H₂O	77

光催化氧化交叉偶联制备对称/不对称硫代磺酸酯

Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates

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