PPh3-Mediated One-Pot Synthesis of Indolin-3-ones from 2-Alkynylnitrobenzenes and Indoles

doi:10.6023/cjoc202506013

Abstract

An efficient method for the preparation of indolin-3-one derivatives from 2-alkynylnitrobenzenes and indoles under alkaline conditions is described. In this reaction, the Wittig process is initiated by PPh₃, and then the indole is activated under the action of the base to offer the indolin-3-one substituted by C(2)-indole in up to 98% yield. A variety of functionalized indolin-3-one derivatives were synthesized by modification of 2-alkynylnitroarenes under transition-metal free conditions.

Key words: PPh₃, Wittig reaction, 2-alkynylnitroarene, indolin-3-one

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Faxiu Feng, Shijie Xu, Xue Wang, Zhuoran Yang, Wenjun Wang, Shenlin Huang, Xiaoxiang Zhang. PPh₃-Mediated One-Pot Synthesis of Indolin-3-ones from 2-Alkynylnitrobenzenes and Indoles[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 225-232.

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References 25

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Entry	Base/equiv.	Solvent	PPh₃/equiv.	2a/equiv.	Yield^b/%
1	K₂CO₃ (3)	CH₃CN	10	5	95
2	DBU (3)	CH₃CN	10	5	27
3	NaOH (3)	CH₃CN	10	5	Trace
4	Cs₂CO₃ (3)	CH₃CN	10	5	80
5	t-BuOK (3)	CH₃CN	10	5	Trace
6	K₂CO₃ (5)	CH₃CN	10	5	97
7	K₂CO₃ (2)	CH₃CN	10	5	89
8	K₂CO₃ (5)	CH₃CN	10	2	90
9	K₂CO₃ (5)	CH₃CN	10	10	97
10	K₂CO₃ (5)	Et₃N	10	5	Trace
11	K₂CO₃ (5)	H₂O	10	5	38
12	K₂CO₃ (5)	DMSO	10	5	25
13	K₂CO₃ (5)	1,4-Dioxane	10	5	13
14^c	K₂CO₃ (5)	CH₃CN	10	5	60
15^d	K₂CO₃ (5)	CH₃CN	10	5	Trace
16	K₂CO₃ (5)	CH₃CN	5	5	78
17^e	K₂CO₃ (5)	CH₃CN	5	5	98
18	—	CH₃CN	5	5	Trace
19	K₂CO₃ (5)	CH₃CN	2	5	55

Entry	Base/equiv.	Solvent	PPh₃/equiv.	2a/equiv.	Yield^b/%
1	K₂CO₃ (3)	CH₃CN	10	5	95
2	DBU (3)	CH₃CN	10	5	27
3	NaOH (3)	CH₃CN	10	5	Trace
4	Cs₂CO₃ (3)	CH₃CN	10	5	80
5	t-BuOK (3)	CH₃CN	10	5	Trace
6	K₂CO₃ (5)	CH₃CN	10	5	97
7	K₂CO₃ (2)	CH₃CN	10	5	89
8	K₂CO₃ (5)	CH₃CN	10	2	90
9	K₂CO₃ (5)	CH₃CN	10	10	97
10	K₂CO₃ (5)	Et₃N	10	5	Trace
11	K₂CO₃ (5)	H₂O	10	5	38
12	K₂CO₃ (5)	DMSO	10	5	25
13	K₂CO₃ (5)	1,4-Dioxane	10	5	13
14^c	K₂CO₃ (5)	CH₃CN	10	5	60
15^d	K₂CO₃ (5)	CH₃CN	10	5	Trace
16	K₂CO₃ (5)	CH₃CN	5	5	78
17^e	K₂CO₃ (5)	CH₃CN	5	5	98
18	—	CH₃CN	5	5	Trace
19	K₂CO₃ (5)	CH₃CN	2	5	55

PPh₃介导2-炔基硝基苯与吲哚一锅法合成吲哚啉-3-酮

PPh₃-Mediated One-Pot Synthesis of Indolin-3-ones from 2-Alkynylnitrobenzenes and Indoles

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PPh3介导2-炔基硝基苯与吲哚一锅法合成吲哚啉-3-酮