Photoinduced Difluoromethylation/Cyclization of 2-Aryl Indoles with HCF2SO2Na

doi:10.6023/cjoc202409008

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (4): 1239-1248.DOI: 10.6023/cjoc202409008 Previous Articles Next Articles

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可见光诱导2-芳基吲哚与二氟甲基亚磺酸钠二氟甲基化/环化反应

蒋洁, 李佳丽, 潘若涵, 陈宇, 刘佳乐, 唐裕才^*()

湖南文理学院化学与材料工程学院水处理功能材料湖南省重点实验室电镀废水回用技术湖南省工程技术研究中心湖南常德 415000

收稿日期:2024-09-09 修回日期:2024-11-08 发布日期:2024-12-05
基金资助:
湖南省教育厅基金(23B0650); 湖南文理学院重点(24ZZ02)

Photoinduced Difluoromethylation/Cyclization of 2-Aryl Indoles with HCF₂SO₂Na

Jie Jiang, Jiali Li, Ruohan Pan, Yu Chen, Jiale Liu, Yucai Tang()

Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology, College of Chemistry and Materials Engineering,Hunan University of Arts and Science, Changde, Hunan 415000

Received:2024-09-09 Revised:2024-11-08 Published:2024-12-05
Contact: * E-mail: yctang1009@163.com
Supported by:
Scientific Research Foundation of Hunan Provincial Education Department(23B0650); Key Research Project of Hunan University of Arts and Sciences(24ZZ02)

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Abstract

Difluoromethyl compounds are widely found in natural products, bioactive molecule and pharmaceuticals. A visible-light induced difluoromethylation/cyclization of 2-aryl indoles is described to construct indolo[2,1-a]isoquinolin-6(5H)-one derivatives using the inexpensive and easy-to-handle HCF₂SO₂Na as an HCF₂ sources. Diverse difluoromethylated indolo[2,1-a]isoquinolines were readily obtained in moderate to good yields. Mechanistic studies demonstrate that the reaction may involve a radical process.

Key words: difluoromethyl compounds, visible-light, 2-aryl indoles, difluoromethylation/cyclization

Cite this article

Jie Jiang, Jiali Li, Ruohan Pan, Yu Chen, Jiale Liu, Yucai Tang. Photoinduced Difluoromethylation/Cyclization of 2-Aryl Indoles with HCF₂SO₂Na[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1239-1248.

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References 16

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Entry	Organic dye	Oxidant	Solvent	Yield^b/%
1	Fluorescein	K₂S₂O₈	DMSO	38
2	Rose Bengal	K₂S₂O₈	DMSO	64
3	Eosin B	K₂S₂O₈	DMSO	70
4	Na₂-EosinY	K₂S₂O₈	DMSO	49
5	Ru(bpy)₃(Cl)₂•6H₂O	K₂S₂O₈	DMSO	62
6	Eosin B	(NH₄)₂S₂O₈	DMSO	55
7	Eosin B	Na₂S₂O₈	DMSO	58
8^c	Eosin B	TBHP	DMSO	29
9	Eosin B	K₂S₂O₈	DMF	49
10	Eosin B	K₂S₂O₈	CH₃CN	Trace
11	Eosin B	K₂S₂O₈	DCE	54
12	Eosin B	K₂S₂O₈	THF	5
13^d	Eosin B	K₂S₂O₈	DMSO	58
14^e	Eosin B	K₂S₂O₈	DMSO	18
15	—	K₂S₂O₈	DMSO	46
16^f	Eosin B	K₂S₂O₈	DMSO	Trace

Entry	Organic dye	Oxidant	Solvent	Yield^b/%
1	Fluorescein	K₂S₂O₈	DMSO	38
2	Rose Bengal	K₂S₂O₈	DMSO	64
3	Eosin B	K₂S₂O₈	DMSO	70
4	Na₂-EosinY	K₂S₂O₈	DMSO	49
5	Ru(bpy)₃(Cl)₂•6H₂O	K₂S₂O₈	DMSO	62
6	Eosin B	(NH₄)₂S₂O₈	DMSO	55
7	Eosin B	Na₂S₂O₈	DMSO	58
8^c	Eosin B	TBHP	DMSO	29
9	Eosin B	K₂S₂O₈	DMF	49
10	Eosin B	K₂S₂O₈	CH₃CN	Trace
11	Eosin B	K₂S₂O₈	DCE	54
12	Eosin B	K₂S₂O₈	THF	5
13^d	Eosin B	K₂S₂O₈	DMSO	58
14^e	Eosin B	K₂S₂O₈	DMSO	18
15	—	K₂S₂O₈	DMSO	46
16^f	Eosin B	K₂S₂O₈	DMSO	Trace

可见光诱导2-芳基吲哚与二氟甲基亚磺酸钠二氟甲基化/环化反应

Photoinduced Difluoromethylation/Cyclization of 2-Aryl Indoles with HCF₂SO₂Na

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