Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes

doi:10.6023/cjoc202102051

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2290-2301.DOI: 10.6023/cjoc202102051 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；热点论文虚拟合集

ARTICLES

可见光催化炔烃串联氰基烷基磺酰化/环化

刘宇^a^,^b, 陈赞^a, 陈镤^a, 熊碧权^a, 谢军^a^,^*(), 刘岸^a^,^*(), 梁云^b, 唐课文^a

a 湖南理工学院化学化工学院湖南岳阳 414006
b 湖南师范大学湖南省有机功能分子组装与应用重点实验室长沙 410081

收稿日期:2021-02-27 修回日期:2021-03-18 发布日期:2021-03-25
通讯作者: 谢军, 刘岸
基金资助:
国家自然科学基金(22078084); 国家自然科学基金(51874132); 湖南省教育厅科学研究基金(20A224); 湖南省教育厅科学研究基金(20A213); 湖南省教育厅科学研究基金(18B355); 湖南省科技计划项目(2020RC3056); 湖南省科技计划项目(2018TP1017); 湖南省自然科学基金(2020JJ5221); 湖南省自然科学基金(2020JJ5212)

Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes

Yu Liu^a^,^b, Zan Chen^a, Pu Chen^a, Biquan Xiong^a, Jun Xie^a(), An Liu^a(), Yun Liang^b, Kewen Tang^a

a Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006
b Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081

Received:2021-02-27 Revised:2021-03-18 Published:2021-03-25
Contact: Jun Xie, An Liu
Supported by:
National Natural Science Foundation of China(22078084); National Natural Science Foundation of China(51874132); Scientific Research Fund of Hunan Provincial Education Department(20A224); Scientific Research Fund of Hunan Provincial Education Department(20A213); Scientific Research Fund of Hunan Provincial Education Department(18B355); Science and Technology Planning Project of Hunan Province(2020RC3056); Science and Technology Planning Project of Hunan Province(2018TP1017); Natural Science Foundation of Hunan Province(2020JJ5221); Natural Science Foundation of Hunan Province(2020JJ5212)

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Abstract

A transition-metal-free visible-light-mediated tandem cyanoalkylsulfonylation/cyclization of alkynes with cycloketone oxime derivatives for the construction of 2-cyanoalkylsulfonyl-9H-pyrrolo[1,2-a]indoles through the insertion of SO₂ is reported. The difunctionalization of carbon-carbon triple bonds includes a radical mechanism and undergoes the formation of iminyl radical, ring-opening of cycloketone, insertion of SO₂, addition of sulfonyl radical to carbon-carbon triple bonds, intramolecular cyclization and isomerization.

Key words: visible-light-catalysis, the insertion of SO₂, cycloketone oxime esters, N-propargylindoles

Cite this article

Yu Liu, Zan Chen, Pu Chen, Biquan Xiong, Jun Xie, An Liu, Yun Liang, Kewen Tang. Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2290-2301.

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可见光催化炔烃串联氰基烷基磺酰化/环化

Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes

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References 21

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Entry	Variation from the standard conditions	Yield/%
1	None	81
2	2a-1 instead of 2a	13
3	2a-2 instead of 2a	25
4	2a-3 instead of 2a	46
5	2a-4 instead of 2a	55
6	2a-5 instead of 2a	51
7	2a-6 instead of 2a	50
8	DABSO instead of K₂S₂O₅	8
9	Thiourea dioxide instead of K₂S₂O₅	67
10^c	Na₂S₂O₅ instead of K₂S₂O₅	73
11^c	Without Na₂-Eosin Y	0
12	Ir(ppy)₃ instead of Na₂-Eosin Y	59
13	Ru(bpy)₃Cl₂ instead of Na₂-Eosin Y	34
14	Eosin Y instead of Na₂-Eosin Y	64
15	Without additional light	0
16	Na₂-Eosin Y (5 mol%)	81
17	Toluene instead of CH₃CN	40
18	THF instead of CH₃CN	38
19^c	DMF instead of CH₃CN	27
20^c	Dioxane instead of CH₃CN	44
21	DMSO instead of CH₃CN	32
22	3 W blue LED light	61
23	12 W blue LED light	54
24	36 W compact fluorescent light	45
25	At 100 ℃	70
26	At 60 ℃	42
27	For 32 h	80
28^d	None	52