Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes

doi:10.6023/cjoc202110041

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1170-1178.DOI: 10.6023/cjoc202110041 Previous Articles Next Articles

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以氢硅烷为氢源: 铱催化N-杂环化合物的氢化

张苗苗, 韩波^*(), 马豪杰, 赵亮, 王记江, 张玉琦^*()

延安大学化学与化工学院新能源新功能材料重点实验室陕西省化学反应工程重点实验室陕西延安 716000

收稿日期:2021-10-29 修回日期:2021-11-26 发布日期:2021-12-15
通讯作者: 韩波, 张玉琦
基金资助:
国家自然科学基金(22061041); 陕西省自然科学基金(2020JQ-789); 陕西省科技资源开放共享平台(2021PT-004); 延安大学博士科研启动经费(YDBK2019-60); 陕西省大学生创新创业训练计划(S202010719114)

Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes

Miaomiao Zhang, Bo Han(), Haojie Ma, Liang Zhao, Jijiang Wang, Yuqi Zhang()

Laboratory of New Energy ＆ New Function Materials, Shaanxi Key Laboratory of Chemical and Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000

Received:2021-10-29 Revised:2021-11-26 Published:2021-12-15
Contact: Bo Han, Yuqi Zhang
Supported by:
National Natural Science Foundation of China(22061041); Natural Science Foundation of Shaanxi Province(2020JQ-789); Open Sharing Platform for Scientific and Technological Resources of Shaanxi Province(2021PT-004); Doctoral Research Foundation of Yan'an University(YDBK2019-60); Training Program of Innovation and Entrepreneurship for Undergraduates of Shaanxi Province(S202010719114)

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Abstract

A ligand- and base-free method for the catalytic synthesis of bioactive 1,2,3,4-tetrahydroquinolines via the homogeneous iridium-catalyzed hydrogenation of quinolines and related N-heteroarenes is reported. A catalytic reduction of N-heteroarenes employing low-cost and air-stable hydrosilane was demonstrated under mild conditions. This reaction is scalable and tolerable for sensitive functional groups, such as bromide, chloride, fluoride, ester, carboxylic acid, cyanogroup and nitro groups. This catalytic system provides a convenient, environmentally friendly and practical method to obtain a variety of 1,2,3,4-tetrahydroquinoline derivatives under mild reaction conditions.

Key words: hydrogenation, N-heteroarenes, iridium, hydrosilane

Cite this article

Miaomiao Zhang, Bo Han, Haojie Ma, Liang Zhao, Jijiang Wang, Yuqi Zhang. Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1170-1178.

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Entry^a	[Si]—H (equiv.)	Solvent	T/℃	of 2a^b/%
1	PMHS (4.0)	MeOH	r.t.	55
2	(EtO)₃SiH (4.0)	MeOH	r.t.	40
3	Et₃SiH (4.0)	MeOH	r.t.	59
4	Ph₃SiH (4.0)	MeOH	r.t.	61
5	Ph₂SiH₂ (4.0)	MeOH	r.t.	66
6	PhSiH₃ (4.0)	MeOH	r.t.	74
7	PhSiH₃ (4.0)	EtOH	r.t.	71
8	PhSiH₃ (4.0)	ⁱPrOH	r.t.	46
9	PhSiH₃ (4.0)	THF	r.t.	39
10	PhSiH₃ (5.0)	MeOH	r.t.	71
11	PhSiH₃ (3.0)	MeOH	r.t.	68
12	PhSiH₃ (2.0)	MeOH	r.t.	39
13	PhSiH₃ (4.0)	MeOH	45	94 (83)^c

Entry^a	[Si]—H (equiv.)	Solvent	T/℃	of 2a^b/%
1	PMHS (4.0)	MeOH	r.t.	55
2	(EtO)₃SiH (4.0)	MeOH	r.t.	40
3	Et₃SiH (4.0)	MeOH	r.t.	59
4	Ph₃SiH (4.0)	MeOH	r.t.	61
5	Ph₂SiH₂ (4.0)	MeOH	r.t.	66
6	PhSiH₃ (4.0)	MeOH	r.t.	74
7	PhSiH₃ (4.0)	EtOH	r.t.	71
8	PhSiH₃ (4.0)	ⁱPrOH	r.t.	46
9	PhSiH₃ (4.0)	THF	r.t.	39
10	PhSiH₃ (5.0)	MeOH	r.t.	71
11	PhSiH₃ (3.0)	MeOH	r.t.	68
12	PhSiH₃ (2.0)	MeOH	r.t.	39
13	PhSiH₃ (4.0)	MeOH	45	94 (83)^c

以氢硅烷为氢源: 铱催化N-杂环化合物的氢化

Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes

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