Iridium-Catalyzed Synthesis of Indole Derivatives from N-Aryl-2-aminopyridines and Vinylene Carbonate

doi:10.6023/cjoc202411025

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 2149-2156.DOI: 10.6023/cjoc202411025 Previous Articles Next Articles

ARTICLES

铱催化N-芳基-2-氨基吡啶和碳酸亚乙烯酯合成吲哚衍生物

梁珍^a^,^†, 徐维焱^a^,^†, 陈毅^a, 邱化玉^a, 赵也哲^b, 沈佳斌^b^,^*(), 王民^a^,^*()

^a 杭州师范大学材料与化学化工学院教育部有机硅化学及材料技术重点实验室杭州 311121
^b 浙江树人学院生物与环境工程学院浙江省污染暴露与健康干预重点实验室杭州 310015

收稿日期:2024-11-29 修回日期:2025-01-13 发布日期:2025-02-14
通讯作者: 沈佳斌, 王民
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22178079)

Iridium-Catalyzed Synthesis of Indole Derivatives from N-Aryl-2-aminopyridines and Vinylene Carbonate

Zhen Liang^a^,^†, Weiyan Xu^a^,^†, Yi Chen^a, Huayu Qiu^a, Yezhe Zhao^b, Jiabin Shen^b^,^*(), Min Wang^a^,^*()

^a Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121
^b Key Laboratory of Pollution Exposure and Health Intervention of Zhejiang Province, College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015

Received:2024-11-29 Revised:2025-01-13 Published:2025-02-14
Contact: Jiabin Shen, Min Wang
About author:
^†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22178079)

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Abstract

Indoles and their derivatives are an important class of N-heterocycles. In this article, iridium-catalyzed annulation reactions of N-aryl-2-aminopyridines to synthesize indole derivatives are designed and developed, which utilize vinylene carbonate as a new C2 synthon. This protocol is expected to provide a facile and useful access to various indole derivatives.

Key words: indoles, iridium-catalyzed, annulation reactions, vinylene carbonate, aminopyridines

Cite this article

Zhen Liang, Weiyan Xu, Yi Chen, Huayu Qiu, Yezhe Zhao, Jiabin Shen, Min Wang. Iridium-Catalyzed Synthesis of Indole Derivatives from N-Aryl-2-aminopyridines and Vinylene Carbonate[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2149-2156.

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References 14

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Entry	Catalyst	Ag salt	Additive	Solvent	Yield^b/%
1	[Cp*RhCl₂]₂	AgSbF₆	PivOH	THF	Trace
2	[Ru(p-cymene)Cl₂]₂	AgSbF₆	PivOH	THF	Trace
3	[Cp*Co(CO)I₂]	AgSbF₆	PivOH	THF	Trace
4	Pd(OAc)₂	AgSbF₆	PivOH	THF	Trace
5	[Cp*IrCl₂]₂	AgSbF₆	PivOH	THF	46
6	[Cp*IrCl₂]₂	AgSbF₆	HOAc	THF	31
7	[Cp*IrCl₂]₂	AgSbF₆	NaOAc	THF	Trace
8	[Cp*IrCl₂]₂	AgSbF₆	Cu(OAc)₂	THF	Trace
9	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	THF	56
10	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	DCE	35
11	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	EA	18
12	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	PhMe	51
13	[Cp*IrCl₂]₂	AgBF₄	Zn(OAc)₂	THF	Trace
14	[Cp*IrCl₂]₂	AgNTf₂	Zn(OAc)₂	THF	73
15	[Cp*IrCl₂]₂	AgOTf	Zn(OAc)₂	THF	54
16^c	[Cp*IrCl₂]₂	AgNTf₂	Zn(OAc)₂	THF	75, 71^d

Entry	Catalyst	Ag salt	Additive	Solvent	Yield^b/%
1	[Cp*RhCl₂]₂	AgSbF₆	PivOH	THF	Trace
2	[Ru(p-cymene)Cl₂]₂	AgSbF₆	PivOH	THF	Trace
3	[Cp*Co(CO)I₂]	AgSbF₆	PivOH	THF	Trace
4	Pd(OAc)₂	AgSbF₆	PivOH	THF	Trace
5	[Cp*IrCl₂]₂	AgSbF₆	PivOH	THF	46
6	[Cp*IrCl₂]₂	AgSbF₆	HOAc	THF	31
7	[Cp*IrCl₂]₂	AgSbF₆	NaOAc	THF	Trace
8	[Cp*IrCl₂]₂	AgSbF₆	Cu(OAc)₂	THF	Trace
9	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	THF	56
10	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	DCE	35
11	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	EA	18
12	[Cp*IrCl₂]₂	AgSbF₆	Zn(OAc)₂	PhMe	51
13	[Cp*IrCl₂]₂	AgBF₄	Zn(OAc)₂	THF	Trace
14	[Cp*IrCl₂]₂	AgNTf₂	Zn(OAc)₂	THF	73
15	[Cp*IrCl₂]₂	AgOTf	Zn(OAc)₂	THF	54
16^c	[Cp*IrCl₂]₂	AgNTf₂	Zn(OAc)₂	THF	75, 71^d

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铱催化N-芳基-2-氨基吡啶和碳酸亚乙烯酯合成吲哚衍生物

Iridium-Catalyzed Synthesis of Indole Derivatives from N-Aryl-2-aminopyridines and Vinylene Carbonate

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