Visible Light-Assisted Photocatalyst-Free Tandem Sulfonylation/ Cyclization for the Synthesis of Oxindoles

doi:10.6023/cjoc202208036

Abstract

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

Cite this article

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

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