ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles

doi:10.6023/cjoc201904036

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2906-2911.DOI: 10.6023/cjoc201904036 Previous Articles Next Articles

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氧鎓离子活化的烯丙基醚原位氧化/脱羧芳构化串联反应:一种合成N-烷基吡咯的新方法

李旭彬^a, 周晨^a, 刘星彤^a, 王腾^b, 虞心红^a^*(), 马红梅^a^*(), 李翠清^b^*()

a 华东理工大学药学院制药工程系制药工程与过程化学教育部工程研究中心上海市新药设计重点实验室生物反应器工程国家重点实验室上海 200237
b 北京石油化工学院化学工程学院北京 102617

收稿日期:2019-04-13 修回日期:2019-05-07 发布日期:2019-05-28
通讯作者: 虞心红,马红梅,李翠清 E-mail:xhyu@ecust.edu.cn;hmma@ecust.edu.cn;licuiqing@bipt.edu.cn
基金资助:
国家自然科学基金(21476078);上海市科学技术委员会(No. 12431900902)

ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles

Li, Xubin^a, Zhou, Chen^a, Liu, Xingtong^a, Wang, Teng^b, Yu, Xinhong^a^*(), Ma, Hongmei^a^*(), Li, Cuiqing^b^*()

a Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, State Key Laboratory of Bioengineering Reactors, School of Pharmacy,East China University of Science & Technology, Shanghai 200237;
b College of Chemical Engineering, Beijing Institute of Petrochemical Technology, Beijing 102617

Received:2019-04-13 Revised:2019-05-07 Published:2019-05-28
Contact: Yu, Xinhong,Ma, Hongmei,Li, Cuiqing E-mail:xhyu@ecust.edu.cn;hmma@ecust.edu.cn;licuiqing@bipt.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(21476078);the Science and Technology Commission of Shanghai Municipality(No. 12431900902)

An ipso-oxidation of allyl ether/decarboxylative aromatization cascade strategy is reported, resulting in the formation of N-alkyl pyrroles via oxocarbenium activation. This transformation, which involves formation of C—N bond and cleavage of C—O bond, provides a novel protocol that furnishes N-alkyl pyrroles in 29%~71% yields with good functional group tolerance.

Key words: oxidation of ether, aromatization, pyrroles, synthetic methods

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Li, Xubin, Zhou, Chen, Liu, Xingtong, Wang, Teng, Yu, Xinhong, Ma, Hongmei, Li, Cuiqing. ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2906-2911.

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Fig. & Tab. 5

References 6

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Entry	Oxidant	Solvent	Additive (equiv.)	Yield^b/%
1	DDQ	Toluene	—	27
2^c	DDQ	Toluene	—	11
3	T⁺?$BF^{-}_{4}$	Toluene	—	19
4	DDQ	PhCl	—	33
5	DDQ	DCE	—	24
6	DDQ	CCl₄	—	18
7	DDQ	THF	—	20
8	DDQ	CHCl₃	—	18
9	DDQ	EtOAc	—	23
10	DDQ	PhCl	InCl₃ (1.0)	6
11	DDQ	PhCl	Phenol (1.0)	38
12	DDQ	PhCl	TEMPO (1.0)	27
13	DDQ	PhCl	Antioxidant 300 (0.5)	41
14	DDQ	PhCl	Antioxidant 300 (1.0)	57
15	DDQ	PhCl	Antioxidant 300 (2.0)	33
16^e	DDQ	PhCl	Antioxidant 300 (1.0)	71^d
17^f	DDQ	PhCl	Antioxidant 300 (1.0)	63^d
18^g	DDQ	PhCl	Antioxidant 300 (1.0)	63^d
19^h	DDQ	PhCl	Antioxidant 300 (1.0)	60^d
20ⁱ	DDQ	PhCl	Antioxidant 300 (1.0)	55^d

Entry	Oxidant	Solvent	Additive (equiv.)	Yield^b/%
1	DDQ	Toluene	—	27
2^c	DDQ	Toluene	—	11
3	T⁺?$BF^{-}_{4}$	Toluene	—	19
4	DDQ	PhCl	—	33
5	DDQ	DCE	—	24
6	DDQ	CCl₄	—	18
7	DDQ	THF	—	20
8	DDQ	CHCl₃	—	18
9	DDQ	EtOAc	—	23
10	DDQ	PhCl	InCl₃ (1.0)	6
11	DDQ	PhCl	Phenol (1.0)	38
12	DDQ	PhCl	TEMPO (1.0)	27
13	DDQ	PhCl	Antioxidant 300 (0.5)	41
14	DDQ	PhCl	Antioxidant 300 (1.0)	57
15	DDQ	PhCl	Antioxidant 300 (2.0)	33
16^e	DDQ	PhCl	Antioxidant 300 (1.0)	71^d
17^f	DDQ	PhCl	Antioxidant 300 (1.0)	63^d
18^g	DDQ	PhCl	Antioxidant 300 (1.0)	63^d
19^h	DDQ	PhCl	Antioxidant 300 (1.0)	60^d
20ⁱ	DDQ	PhCl	Antioxidant 300 (1.0)	55^d

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氧鎓离子活化的烯丙基醚原位氧化/脱羧芳构化串联反应:一种合成N-烷基吡咯的新方法

ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles

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