1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives

doi:10.6023/cjoc202109026

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 796-802.DOI: 10.6023/cjoc202109026 Previous Articles Next Articles

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可回收铋配合物催化氮亲核试剂与对醌甲基化物1,6-加成:轻松获得N-杂环取代的不对称三芳基甲烷衍生物

刘冬兰, 许海燕^*(), 杭懿, 陆鸿飞^*()

江苏科技大学环境与化学工程学院江苏镇江 212100

收稿日期:2021-09-17 修回日期:2021-11-08 发布日期:2021-11-25
通讯作者: 许海燕, 陆鸿飞
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21901087); 江苏省自然科学基金(BK20190591)

1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives

Donglan Liu, Haiyan Xu(), Yi Hang, Hongfei Lu()

School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212100

Received:2021-09-17 Revised:2021-11-08 Published:2021-11-25
Contact: Haiyan Xu, Hongfei Lu
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21901087); Natural Science Foundation of Jiangsu Province(BK20190591)

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Abstract

A useful protocol for the synthesis of nitrogen-containing unsymmetric triarylmethane derivatives through 1,6-aza-Michael addition of para-quinone methides (p-QMs) and various aromatic N-heterocycles was developed. This established synthetic strategy features mild reaction conditions, acceptable catalyst loading, atom economy, easy scale-up and enables the formation of N-heterocyclic-substituted unsymmetric triarylmethane derivatives in moderate to excellent yields. Moreover, the bismuth catalyst can be reused several times without losing of its activity.

Key words: recyclable bismuth catalyst, N-heterocyclic-substituted unsymmetric triarylmethane derivatives, para-quinone methide, 1,6-Michael addition reaction

Cite this article

Donglan Liu, Haiyan Xu, Yi Hang, Hongfei Lu. 1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 796-802.

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Fig. & Tab. 7

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Entry	Catalyst	Solvent	Yield^b/%
1	—	CH₃CN	trace
2^c	[Bi]	CH₃CN	91
3	BiCl₃	CH₃CN	80
4	Bi(OTf)₃	CH₃CN	82
5	FeCl₃	CH₃CN	86
6	AlCl₃	CH₃CN	85
7	Sc(OTf)₃	CH₃CN	82
8	Ni(OTf)₂	CH₃CN	14
9	Zn(OTf)₂	CH₃CN	87
10	[Bi]	MeOH	55
11	[Bi]	1,4-Dioxane	77
12	[Bi]	Toluene	10
13	[Bi]	DCM	85
14	[Bi] (1 mol%)	CH₃CN	80

Entry	Catalyst	Solvent	Yield^b/%
1	—	CH₃CN	trace
2^c	[Bi]	CH₃CN	91
3	BiCl₃	CH₃CN	80
4	Bi(OTf)₃	CH₃CN	82
5	FeCl₃	CH₃CN	86
6	AlCl₃	CH₃CN	85
7	Sc(OTf)₃	CH₃CN	82
8	Ni(OTf)₂	CH₃CN	14
9	Zn(OTf)₂	CH₃CN	87
10	[Bi]	MeOH	55
11	[Bi]	1,4-Dioxane	77
12	[Bi]	Toluene	10
13	[Bi]	DCM	85
14	[Bi] (1 mol%)	CH₃CN	80

可回收铋配合物催化氮亲核试剂与对醌甲基化物1,6-加成:轻松获得N-杂环取代的不对称三芳基甲烷衍生物

1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives

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