Trimethylsilyl Bromide-Induced Regioselective Dimerization of N-Protected Indoles to 2,3'-Linked Indolylindolines

doi:10.6023/cjoc202109011

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4758-4765.DOI: 10.6023/cjoc202109011 Previous Articles Next Articles

Special Issue: 绿色合成化学专辑；热点论文虚拟合集

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三甲基溴硅烷诱导的N-保护吲哚的区域选择性二聚合成2,3′-吲哚基二氢吲哚

唐爱玲, 金伟伟^*(), 刘晨江^*()

新疆大学化学学院乌鲁木齐 830046

收稿日期:2021-09-06 修回日期:2021-10-19 发布日期:2021-11-03
通讯作者: 金伟伟, 刘晨江
基金资助:
国家自然科学基金(21572195); 国家自然科学基金(21702175); 国家自然科学基金(21961037)

Trimethylsilyl Bromide-Induced Regioselective Dimerization of N-Protected Indoles to 2,3'-Linked Indolylindolines

Ailing Tang, Weiwei Jin(), Chenjiang Liu()

College of Chemistry, Xinjiang University, Urumqi 830046

Received:2021-09-06 Revised:2021-10-19 Published:2021-11-03
Contact: Weiwei Jin, Chenjiang Liu
Supported by:
National Natural Science Foundation of China(21572195); National Natural Science Foundation of China(21702175); National Natural Science Foundation of China(21961037)

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Abstract

A dimerization of N-methylindoles by trimethylsilyl bromide promoted C—C bond cross coupling reactions is described. A series of 2,3'-linked indolylindolines are smoothly installed under mild reaction conditions with up to 95% yields. The gram scale reactions demonstrate the practicality of this protocol. The UV-vis absorption and fluorescence spectra properties of target products are preliminarily studied.

Key words: indole, dimerization, cross-coupling, indolylindoline

Cite this article

Ailing Tang, Weiwei Jin, Chenjiang Liu. Trimethylsilyl Bromide-Induced Regioselective Dimerization of N-Protected Indoles to 2,3'-Linked Indolylindolines[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4758-4765.

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Fig. & Tab. 8

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Entry	Base	Solvent	Additive	Yield of 2a^b/%
1	K₂CO₃	DCM	TMSCl	61
2	KOH	DCM	TMSCl	24
3	K₃PO₄•3H₂O	DCM	TMSCl	63
4	K₃PO₄•3H₂O	CHCl₃	TMSCl	59
5	K₃PO₄•3H₂O	DCM/CHCl₃	TMSCl	68
6	K₃PO₄•3H₂O	DCM/CHCl₃	TfOH	50
7	K₃PO₄•3H₂O	DCM/CHCl₃	TMSOTf	55
8	K₃PO₄•3H₂O	DCM/CHCl₃	TMSI	29
9	K₃PO₄•3H₂O	DCM/CHCl₃	TMSBr	79
10^c	K₃PO₄•3H₂O	DCM/CHCl₃	TMSBr	35
11^d	K₃PO₄•3H₂O	DCM/CHCl₃	TMSBr	78
12	—	DCM/CHCl₃	TMSBr	n.r.
13	K₃PO₄•3H₂O	DCM/CHCl₃	—	n.r.

Entry	Base	Solvent	Additive	Yield of 2a^b/%
1	K₂CO₃	DCM	TMSCl	61
2	KOH	DCM	TMSCl	24
3	K₃PO₄•3H₂O	DCM	TMSCl	63
4	K₃PO₄•3H₂O	CHCl₃	TMSCl	59
5	K₃PO₄•3H₂O	DCM/CHCl₃	TMSCl	68
6	K₃PO₄•3H₂O	DCM/CHCl₃	TfOH	50
7	K₃PO₄•3H₂O	DCM/CHCl₃	TMSOTf	55
8	K₃PO₄•3H₂O	DCM/CHCl₃	TMSI	29
9	K₃PO₄•3H₂O	DCM/CHCl₃	TMSBr	79
10^c	K₃PO₄•3H₂O	DCM/CHCl₃	TMSBr	35
11^d	K₃PO₄•3H₂O	DCM/CHCl₃	TMSBr	78
12	—	DCM/CHCl₃	TMSBr	n.r.
13	K₃PO₄•3H₂O	DCM/CHCl₃	—	n.r.

Entry	Radical scavengers (2 equiv.)	Yield/%
1	BHT	95
2	1,1-Diphenylethylene	66
3	Standard conditions	79

Entry	Radical scavengers (2 equiv.)	Yield/%
1	BHT	95
2	1,1-Diphenylethylene	66
3	Standard conditions	79

三甲基溴硅烷诱导的N-保护吲哚的区域选择性二聚合成2,3′-吲哚基二氢吲哚

Trimethylsilyl Bromide-Induced Regioselective Dimerization of N-Protected Indoles to 2,3'-Linked Indolylindolines

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