可见光辅助无光敏剂串联磺酰化-环化合成吲哚酮

doi:10.6023/cjoc202208036

摘要/Abstract

吲哚酮类的衍生物在许多领域具有重要应用, 这种特殊的杂环骨架以其独特的功能性在天然产物和生物活性分子中的应用越来越广泛. 因此探索新型的吲哚酮衍生物的合成方法非常重要. 报道了一种在可见光辅助下无光敏剂的磺酰化吲哚酮的高效合成方法. 该方法从简单易得的N-芳基丙烯酰胺和芳基或烷基亚磺酸钠出发, 使用廉价的K₂S₂O₈作为氧化剂, 具有中等至良好的产率及出色的官能团耐受性.

关键词: 可见光诱导, N-芳基丙烯酰胺, 吲哚酮, 环化

Oxindole derivatives are well developed in many fields, and this special heterocyclic scaffold is more and more widely used in natural products and bioactive molecules due to its unique functionality. Therefore, it is very important to explore new synthesis methods for this motif. A visible light-assisted photocatalyst-free protocol for the efficient synthesis of sulfonylated oxindoles under mild condition was reported. The present method starts from simple and readily available N-arylacrylamide and sodium sulfinates, uses cheap K₂S₂O₈ as oxidant, and features moderate to good yields and excellent functional group tolerance.

Key words: photocatalysis, N-arylacrylamide, oxindole, cyclization, photocatalyst-free

引用此文

巫晓婷, 赵峰, 姬小趁, 黄华文. 可见光辅助无光敏剂串联磺酰化-环化合成吲哚酮[J]. 有机化学, 2022, 42(12): 4323-4331.

Xiaoting Wu, Feng Zhao, Xiaochen Ji, Huawen Huang. Visible Light-Assisted Photocatalyst-Free Tandem Sulfonylation/ Cyclization for the Synthesis of Oxindoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4323-4331.

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Entry	Photocatalyst	Additive	Oxidant	Aolvent	Yield^a/%
1	[Ir]PF₆	KI	Air	MeOH	10
2	[Ir]PF₆	KI	K₂S₂O₈	MeOH	59
3	[Ir]PF₆	KI	TBHP	MeOH	30
4	[Ir]PF₆	KI	DTBP	MeOH	25
5	[Ir]PF₆	NaI	K₂S₂O₈	MeOH	30
6	[Ir]PF₆	LiBr	K₂S₂O₈	MeOH	10
7	[Ir]PF₆	NaBr	K₂S₂O₈	MeOH	Trace
8	[Ir]PF₆	KI	K₂S₂O₈	MeCN	45
9	[Ir]PF₆	KI	K₂S₂O₈	DMSO	30
10	[Ir]PF₆	KI	K₂S₂O₈	Acetone	27
11 12^b	[Ir]PF₆ [Ir]PF₆	KI KI	K₂S₂O₈ K₂S₂O₈	THF MeOH	25 16
13^c	[Ir]PF₆	KI	K₂S₂O₈	MeOH	89
14^c	—	KI	K₂S₂O₈	MeOH	90
15^c	—	—	K₂S₂O₈	MeOH	33
16	—	KI	—	MeOH	Trace
17^d	—	KI	K₂S₂O₈	MeOH	39
18^d^,^e	—	KI	K₂S₂O₈	MeOH	41
19^f	—	—	—	MeOH	28
20^g	—	KI	K₂S₂O₈	MeOH	65

Entry	Photocatalyst	Additive	Oxidant	Aolvent	Yield^a/%
1	[Ir]PF₆	KI	Air	MeOH	10
2	[Ir]PF₆	KI	K₂S₂O₈	MeOH	59
3	[Ir]PF₆	KI	TBHP	MeOH	30
4	[Ir]PF₆	KI	DTBP	MeOH	25
5	[Ir]PF₆	NaI	K₂S₂O₈	MeOH	30
6	[Ir]PF₆	LiBr	K₂S₂O₈	MeOH	10
7	[Ir]PF₆	NaBr	K₂S₂O₈	MeOH	Trace
8	[Ir]PF₆	KI	K₂S₂O₈	MeCN	45
9	[Ir]PF₆	KI	K₂S₂O₈	DMSO	30
10	[Ir]PF₆	KI	K₂S₂O₈	Acetone	27
11 12^b	[Ir]PF₆ [Ir]PF₆	KI KI	K₂S₂O₈ K₂S₂O₈	THF MeOH	25 16
13^c	[Ir]PF₆	KI	K₂S₂O₈	MeOH	89
14^c	—	KI	K₂S₂O₈	MeOH	90
15^c	—	—	K₂S₂O₈	MeOH	33
16	—	KI	—	MeOH	Trace
17^d	—	KI	K₂S₂O₈	MeOH	39
18^d^,^e	—	KI	K₂S₂O₈	MeOH	41
19^f	—	—	—	MeOH	28
20^g	—	KI	K₂S₂O₈	MeOH	65