无金属下异腈的膦酰化串联环化反应合成2-膦酰基吲哚

doi:10.6023/cjoc202503002

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3856-3865.DOI: 10.6023/cjoc202503002 上一篇下一篇

研究论文

无金属下异腈的膦酰化串联环化反应合成2-膦酰基吲哚

曹锐锋^a^,^†, 肖蔺^a^,^†, 龙天宇^a^,^b^,^†, 古家侗^a, 李杨华^c, 孔晗晗^a^,^*(), 阳青青^a, 黄年玉^d, 王龙^a^,^e^,^*()

^a 三峡大学材料与化工学院无机非金属晶态与能源转换材料重点实验室湖北宜昌 443002
^b 三峡大学水利与环境学院湖北宜昌 443002
^c 湖北普瑞提化工科技有限公司湖北宜昌 443200
^d 三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室湖北宜昌 443002
^e 湖北三峡实验室湖北宜昌 443007

收稿日期:2025-03-03 修回日期:2025-04-27 发布日期:2025-05-20
作者简介:
^† 共同第一作者.
基金资助:
国家自然科学基金(22301160); 国家自然科学基金(21702121); 国家自然科学基金(21602123); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2025AFA116); 湖北省自然科学基金(2025AFD270); 湖北省自然科学基金(2023AFB026); 中国博士后科学基金(2023M742043); 湖北三峡实验室基金(SC240014); 湖北三峡实验室基金(SC232008); 湖北三峡实验室基金(SC213008); 及天然产物研究与利用湖北省重点实验室基金(2024NPRD08); 及天然产物研究与利用湖北省重点实验室基金(2022NPRD04)

Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles

Ruifeng Cao^a, Lin Xiao^a, Tianyu Long^a^,^b, Jiadong Gu^a, Yanghua Li^c, Han-Han Kong^a^,^*(), Qing-Qing Yang^a, Nianyu Huang^d, Long Wang^a^,^e^,^*()

^a Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
^b College of Hydraulic and Environmental Engineering, China Three Gorges University, Yichang, Hubei 443002
^c Hubei Pretty Chemical Technology Co., Ltd., Yichang, Hubei 443200
^d Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Science, China Three Gorges University, Yichang, Hubei 443002
^e Hubei Three Gorges Laboratory, Yichang, Hubei 443007

Received:2025-03-03 Revised:2025-04-27 Published:2025-05-20
Contact: * konghanhan@ctgu.edu.cn; wanglongchem@ctgu.edu.cn
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22301160); National Natural Science Foundation of China(21702121); National Natural Science Foundation of China(21602123); Programme of Introducing Talents of Discipline to Universities (111 Project(D20015); Natural Science Foundation of Hubei Province(2025AFA116); Natural Science Foundation of Hubei Province(2025AFD270); Natural Science Foundation of Hubei Province(2023AFB026); China Postdoctoral Science Foundation(2023M742043); Hubei Three Gorges Laboratory Foundation(SC240014); Hubei Three Gorges Laboratory Foundation(SC232008); Hubei Three Gorges Laboratory Foundation(SC213008); Foundation of Hubei Key Laboratory of Natural Products Research and Development(2024NPRD08); Foundation of Hubei Key Laboratory of Natural Products Research and Development(2022NPRD04)

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摘要/Abstract

基于P中心阴离子与2-异氰基苯甲醛的亲核加成-串联环化反应, 开发了一种高效合成2-膦酰基吲哚化合物的方法. 该方法独特地采用碱促进活化, 不需要金属、光或电能, 为膦功能化吲哚的合成提供了创新性解决方案.

关键词: 无金属, 2-膦酰基吲哚, 2-异氰基苯甲醛, P-中心阴离子, 亲核加成反应

A novel approach for the efficient synthesis of 2-phosphinoylindoles has been devised through P-centered anion nucleophilic addition to 2-isocyanobenzaldehydes, followed by cascade cyclization. This method uniquely employs base- promoted activation without requiring metals, light, or electrical energy, thereby offering a metal-free strategy for constructing phosphine-functionalized indoles.

Key words: metal-free, 2-phosphinoylindole, 2-isocyanobenzaldehyde, P-centered anion, nucleophilic addition

引用此文

曹锐锋, 肖蔺, 龙天宇, 古家侗, 李杨华, 孔晗晗, 阳青青, 黄年玉, 王龙. 无金属下异腈的膦酰化串联环化反应合成2-膦酰基吲哚[J]. 有机化学, 2025, 45(10): 3856-3865.

Ruifeng Cao, Lin Xiao, Tianyu Long, Jiadong Gu, Yanghua Li, Han-Han Kong, Qing-Qing Yang, Nianyu Huang, Long Wang. Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3856-3865.

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图/表 8

Figure 1. Representative biologically active compounds and ligands containing phosphinoylindoles skeleton

Scheme 1. Previous reports on the synthesis of 2-phosphinoyl indoles and our work

Entry	Base	Solvent	Yield^b/%
1	DBU	CH₂Cl₂	55
2	DBU	DMSO	67
3	DBU	Toluene	31
4	DBU	MeCN	73
5	DABCO	MeCN	N.D.
6	TMG	MeCN	69
7	t-BuOK	MeCN	51
8	Na₂CO₃	MeCN	N.D.
9^c	DBU	MeCN	76
10^c^,^d	DBU	MeCN	N.D.
11^c^,^e	DBU	MeCN	85
12^c^,^f	DBU	MeCN	74
13^c^,^e^,^g	DBU	MeCN	84 (87)^h

Table 1. Optimization of the reaction conditionsa

Table 2. Substrate scope of 2-phosphonyl indolesa,b

Scheme 2. Gram-scale synthesis and synthetic transformations

Entry	Variation of reaction condition	Yield^b/%
1	—	87
2	w/o base	0
3	TEMPO (5.0 equiv.)	84
4	BHT (5.0 equiv.)	82

Table 3. Control experimenta

Scheme 3. Mechanism experiment

Scheme 4. Plausible reaction mechanism

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无金属下异腈的膦酰化串联环化反应合成2-膦酰基吲哚

Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles

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