Visible-Light Photoredox-Catalyzed Reductive Dearomatization of Indoles

doi:10.6023/cjoc202512044

Abstract

An efficient photoredox catalytic system for the radical reductive dearomatization of indoles is developed. Employing N,N-diisopropylethylamine (DIPEA) as an organic reductant, the reaction proceeds under mild conditions. Both substituted and unsubstituted indoles at the 2-position are well tolerated, affording a series of structurally diverse functiona- lized indoline derivatives in high yields (up to 99%). This method exhibits good functional group compatibility and broad substrate scope. Furthermore, scale-up experiments and synthetic transformations demonstrate the potential utility of this strategy in practical synthesis.

Key words: photoredox, indole, dearomatization, indoline, radical

Cite this article

Dan Yang, Tianzhen Li, Jingyi Bai, Honghao Zhang, Feng Shi. Visible-Light Photoredox-Catalyzed Reductive Dearomatization of Indoles[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1699-1712.

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Entry	PC	Solvent	T/℃	Base	Yield/%
1	I	PhCF₃	50	Cs₂CO₃	25
2	I	DCE	50	Cs₂CO₃	47
3	I	MeCN	50	Cs₂CO₃	50
4	I	THF	50	Cs₂CO₃	20
5	I	DMF	50	Cs₂CO₃	24
6	I	DMAc	50	Cs₂CO₃	15
7	II	MeCN	50	Cs₂CO₃	73
8	III	MeCN	50	Cs₂CO₃	87
9	IV	MeCN	50	Cs₂CO₃	15
10	V	MeCN	50	Cs₂CO₃	32
11	III	MeCN	50	K₂CO₃	93
12	III	MeCN	50	KHCO₃	82
13	III	MeCN	50	K₂HPO₄	79
14	III	MeCN	50	KH₂PO₄	91
15	III	MeCN	50	Cs₂CO₃	88
16	III	MeCN	50	CsF	80
17	III	MeCN	50	K₃PO₄	85
18	III	MeCN	50	—	99
19	III	MeCN	r.t.	—	76

Entry	PC	Solvent	T/℃	Base	Yield/%
1	I	PhCF₃	50	Cs₂CO₃	25
2	I	DCE	50	Cs₂CO₃	47
3	I	MeCN	50	Cs₂CO₃	50
4	I	THF	50	Cs₂CO₃	20
5	I	DMF	50	Cs₂CO₃	24
6	I	DMAc	50	Cs₂CO₃	15
7	II	MeCN	50	Cs₂CO₃	73
8	III	MeCN	50	Cs₂CO₃	87
9	IV	MeCN	50	Cs₂CO₃	15
10	V	MeCN	50	Cs₂CO₃	32
11	III	MeCN	50	K₂CO₃	93
12	III	MeCN	50	KHCO₃	82
13	III	MeCN	50	K₂HPO₄	79
14	III	MeCN	50	KH₂PO₄	91
15	III	MeCN	50	Cs₂CO₃	88
16	III	MeCN	50	CsF	80
17	III	MeCN	50	K₃PO₄	85
18	III	MeCN	50	—	99
19	III	MeCN	r.t.	—	76

Entry	PC	Yield/%
1	III	40
2	I	95
3	II	2
4	IV	43
5	V	60

Entry	PC	Yield/%
1	III	40
2	I	95
3	II	2
4	IV	43
5	V	60

可见光氧化还原催化吲哚的还原去芳构化反应