Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates

doi:10.6023/cjoc202305024

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4268-4276.DOI: 10.6023/cjoc202305024 Previous Articles Next Articles

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可见光促进有机染料催化2-芳基吲哚自由基烷氧羰基化反应研究

杜昌远, 唐裕才^*(), 段京林, 杨碧玉, 何宇鹏, 周谦, 刘学文

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研究中心湖南常德 415000

收稿日期:2023-05-17 修回日期:2023-07-04 发布日期:2023-07-27
基金资助:
湖南省自然科学基金(2020JJ5390); 湖南省自然科学基金(2022JJ30418); 湖南文理学院科学研究(21ZD07); 大学生创新创业训练计划(XDC202318)

Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates

Changyuan Du, Yucai Tang^*(), Jinglin Duan, Biyu Yang, Yupeng He, Qian Zhou, Xuewen Liu

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:2023-05-17 Revised:2023-07-04 Published:2023-07-27
Contact: *E-mail: yctang1009@163.com
Supported by:
Hunan Provincial Natural Science Foundation of China(2020JJ5390); Hunan Provincial Natural Science Foundation of China(2022JJ30418); Key Research Project of Hunan University of Arts and Science(21ZD07); Innovation and Entrepreneurship Training Program for College Students(XDC202318)

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Abstract

A visible-light-mediated organic dye photoredox-catalyzed alkoxycarbonylation of 2-aryl-N-acryloyl indoles to give valuable indolo[2,1-a]isoquinoline derivatives has been developed. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in moderate to good yields. Mild reaction conditions, metal free, visible light as a traceless energy source, economical and environmentally benign Rose Bengal as the catalyst, stable and easily accessible starting materials all make this methodology more attractive.

Key words: Rose Bengal, organic dye, visible-light, 2-aryl-indoles, indolo[2,1-a]isoquinolines

Cite this article

Changyuan Du, Yucai Tang, Jinglin Duan, Biyu Yang, Yupeng He, Qian Zhou, Xuewen Liu. Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4268-4276.

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Fig. & Tab. 6

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Entry	Catalyst	Oxidant	Solvent	Yield^b/%
1	Fluorescein	(NH₄)₂S₂O₈	DMSO	10
2	Na₂-EosinY	(NH₄)₂S₂O₈	DMSO	15
3	Ru(bpy)₃(Cl)₂•6H₂O	(NH₄)₂S₂O₈	DMSO	5
4	Rose Bengal	(NH₄)₂S₂O₈	DMSO	52
5	Eosin B	(NH₄)₂S₂O₈	DMSO	38
6	Rose Bengal	(NH₄)₂S₂O₈	DCE	Trace
7	Rose Bengal	(NH₄)₂S₂O₈	THF	25
8	Rose Bengal	(NH₄)₂S₂O₈	DMF	30
9	Rose Bengal	(NH₄)₂S₂O₈	CH₃CN	Trace
10	Rose Bengal	K₂S₂O₈	DMSO	46
11^c	Rose Bengal	TBHP	DMSO	18
12^d	Rose Bengal	BPO	DMSO	25
13^e	Rose Bengal	DTBP	DMSO	0
14^f	Rose Bengal	(NH₄)₂S₂O₈	DMSO	46
15^g	Rose Bengal	(NH₄)₂S₂O₈	DMSO	35
16^h	Rose Bengal	(NH₄)₂S₂O₈	DMSO	40
17ⁱ	Rose Bengal	(NH₄)₂S₂O₈	DMSO	44
18^j	Rose Bengal	(NH₄)₂S₂O₈	DMSO	0
19^k	—	(NH₄)₂S₂O₈	DMSO	16

Entry	Catalyst	Oxidant	Solvent	Yield^b/%
1	Fluorescein	(NH₄)₂S₂O₈	DMSO	10
2	Na₂-EosinY	(NH₄)₂S₂O₈	DMSO	15
3	Ru(bpy)₃(Cl)₂•6H₂O	(NH₄)₂S₂O₈	DMSO	5
4	Rose Bengal	(NH₄)₂S₂O₈	DMSO	52
5	Eosin B	(NH₄)₂S₂O₈	DMSO	38
6	Rose Bengal	(NH₄)₂S₂O₈	DCE	Trace
7	Rose Bengal	(NH₄)₂S₂O₈	THF	25
8	Rose Bengal	(NH₄)₂S₂O₈	DMF	30
9	Rose Bengal	(NH₄)₂S₂O₈	CH₃CN	Trace
10	Rose Bengal	K₂S₂O₈	DMSO	46
11^c	Rose Bengal	TBHP	DMSO	18
12^d	Rose Bengal	BPO	DMSO	25
13^e	Rose Bengal	DTBP	DMSO	0
14^f	Rose Bengal	(NH₄)₂S₂O₈	DMSO	46
15^g	Rose Bengal	(NH₄)₂S₂O₈	DMSO	35
16^h	Rose Bengal	(NH₄)₂S₂O₈	DMSO	40
17ⁱ	Rose Bengal	(NH₄)₂S₂O₈	DMSO	44
18^j	Rose Bengal	(NH₄)₂S₂O₈	DMSO	0
19^k	—	(NH₄)₂S₂O₈	DMSO	16

可见光促进有机染料催化2-芳基吲哚自由基烷氧羰基化反应研究

Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates

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