Ru(II)-Catalyzed Regioselective C—H Alkenylation of Indoles Using Cyanomethyl Directing Group

doi:10.6023/cjoc202203017

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2192-2200.DOI: 10.6023/cjoc202203017 Previous Articles Next Articles

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氰甲基导向的吲哚选择性C—H烯基化

闫法超^a^,^b, 李洋^a^,^b, 李玉东^a, Mohamed Makha^a, 李跃辉^a^,^*()

^a中国科学院兰州化学物理研究所苏州研究院羰基合成与选择氧化国家重点实验室兰州 730000
^b中国科学院大学北京 100049

收稿日期:2022-03-06 修回日期:2022-03-22 发布日期:2022-08-09
通讯作者: 李跃辉
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22022204); 国家自然科学基金(21633013); 国家自然科学基金(22072167)

Ru(II)-Catalyzed Regioselective C—H Alkenylation of Indoles Using Cyanomethyl Directing Group

Fachao Yan^a^,^b, Yang Li^a^,^b, Yudong Li^a, Mohamed Makha^a, Yuehui Li^a()

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000
^bUniversity of Chinese Academy of Sciences, Beijing 100049

Received:2022-03-06 Revised:2022-03-22 Published:2022-08-09
Contact: Yuehui Li
About author:
^† These authors contributed equally to this work
Supported by:
the National Natural Science Foundation of China(22022204); the National Natural Science Foundation of China(21633013); the National Natural Science Foundation of China(22072167)

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Abstract

A ruthenium-catalyzed C(2)-alkenylation of indole derivatives by employing cyanomethyl as the directing group was developed for the first time. Site-selective alkenylation was achieved for a broad scope of alkenes as coupling partners with a large number of indoles bearing synthetically useful functional groups. The protocol represents a novel method for C(2)-alkenylation of indoles affording biologically relevant indolic compounds. The reaction conditions were mild and it showed good substrate scope and functional group compatibility. Ester group, cyano group, iodine, bromine, fluorine and trifluoromethyl were all well compatible. The directing group can be easily removed under relatively mild conditions to form N—H indoles.

Key words: Ru(II)-catalysis, C(2)-alkenylation, indole, cyanomethyl directing group, C—H bond functionalization

Cite this article

Fachao Yan, Yang Li, Yudong Li, Mohamed Makha, Yuehui Li. Ru(II)-Catalyzed Regioselective C—H Alkenylation of Indoles Using Cyanomethyl Directing Group[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2192-2200.

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Entry	Catalyst	[Ag]	Additive	Yield^b/%
1	[RuCl₂(p-cymene)]₂	AgSbF₆	—	30
2	Ru(OAc)₂(p-cymene)	AgSbF₆	—	11
3	Pd(OAc)₂	AgSbF₆	—	2
4	[Rh(COD)Cl]₂	AgSbF₆	—	Trace
5	[Cp*Co(CO)I₂]	AgSbF₆	—	n.d.
6	Mn(CO)₅Br	AgSbF₆	—	n.d.
7	[RuCl₂(p-cymene)]₂	AgSbF₆	KOAc	24
8	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	52
9	[RuCl₂(p-cymene)]₂	AgPF₆	DABCO	31
10	[RuCl₂(p-cymene)]₂	AgOTf	DABCO	35
11^c	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	58
12^c^,^d	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	80
13^c^,^d^,^e	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	26
14^c^,^d^,^f	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	3
15^c^,^d^,^g	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	n.d.
16^c	—	AgSbF₆	DABCO	n.d.

Entry	Catalyst	[Ag]	Additive	Yield^b/%
1	[RuCl₂(p-cymene)]₂	AgSbF₆	—	30
2	Ru(OAc)₂(p-cymene)	AgSbF₆	—	11
3	Pd(OAc)₂	AgSbF₆	—	2
4	[Rh(COD)Cl]₂	AgSbF₆	—	Trace
5	[Cp*Co(CO)I₂]	AgSbF₆	—	n.d.
6	Mn(CO)₅Br	AgSbF₆	—	n.d.
7	[RuCl₂(p-cymene)]₂	AgSbF₆	KOAc	24
8	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	52
9	[RuCl₂(p-cymene)]₂	AgPF₆	DABCO	31
10	[RuCl₂(p-cymene)]₂	AgOTf	DABCO	35
11^c	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	58
12^c^,^d	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	80
13^c^,^d^,^e	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	26
14^c^,^d^,^f	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	3
15^c^,^d^,^g	[RuCl₂(p-cymene)]₂	AgSbF₆	DABCO	n.d.
16^c	—	AgSbF₆	DABCO	n.d.

氰甲基导向的吲哚选择性C—H烯基化

Ru(II)-Catalyzed Regioselective C—H Alkenylation of Indoles Using Cyanomethyl Directing Group

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