Palladium-Catalyzed Domino Heck/Intermolecular Cross Coupling Reaction for the Synthesis of 3-Alkyl Substituted Indene Derivatives

doi:10.6023/cjoc202407029

Abstract

Indene derivatives are one of the core skeletons of many natural products and drugs, and are widely used in medicine, materials and other fields. It is of great significance to develop a simple and efficient method for the synthesis of indene derivatives. In this work, iodobenzenes with proximity linking unactivated olefins undergo palladium-catalyzed intramolecular Heck reaction to generate alkylpalladium(II) intermediates, which induce the intramolecular nucleophilic cyclization of 2-(2-phenylethynyl)phenylmalonate diethyl ester to afford a series of 3-alkyl substituted indene derivatives. The reaction has the advantages of mild conditions, simple operation, high yield and wide applicability of substrates, which provides a new strategy for the synthesis of indene derivatives.

Key words: palladium catalysis, indene derivatives, Heck reaction

Cite this article

Tuanli Yao, Linlin Wang, Tao Li. Palladium-Catalyzed Domino Heck/Intermolecular Cross Coupling Reaction for the Synthesis of 3-Alkyl Substituted Indene Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1342-1351.

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Entry	Catalyst	Solvent	Base	Temp./℃	Yield/%
1	Pd(PPh₃)₄	THF	K₂CO₃	80	49
2	Pd(PPh₃)₄	Toluene	K₂CO₃	80	N.R.
3	Pd(PPh₃)₄	1,4-Dioxane	K₂CO₃	80	N.R.
4	Pd(PPh₃)₄	MTBE	K₂CO₃	80	Trace
5	Pd(PPh₃)₄	EtOAc	K₂CO₃	80	Trace
6	Pd(PPh₃)₄	DMSO	K₂CO₃	80	Trace
7	Pd(PPh₃)₄	DME	K₂CO₃	80	Trace
8	Pd(PPh₃)₄	DMF	K₂CO₃	80	76
9	Pd(PPh₃)₄	DMA	K₂CO₃	80	91
10	Pd(PPh₃)₄	DMA	K₃PO₄	80	64
11	Pd(PPh₃)₄	DMA	Cs₂CO₃	80	69
12	Pd(PPh₃)₄	DMA	Na₂CO₃	80	67
13	Pd(PPh₃)₄	DMA	t-BuONa	80	N.R.
14	Pd(dba)₂	DMA	K₂CO₃	80	61
15	Pd(PPh₃)₂Cl₂	DMA	K₂CO₃	80	77
16	PdBr₂	DMA	K₂CO₃	80	90
17	Pd(OAc)₂	DMA	K₂CO₃	80	91
18^b	Pd(OAc)₂	DMA	K₂CO₃	80	80
19	Pd(PPh₃)₄	DMA	K₂CO₃	100	87
20	Pd(PPh₃)₄	DMF	K₂CO₃	100	96

Entry	Catalyst	Solvent	Base	Temp./℃	Yield/%
1	Pd(PPh₃)₄	THF	K₂CO₃	80	49
2	Pd(PPh₃)₄	Toluene	K₂CO₃	80	N.R.
3	Pd(PPh₃)₄	1,4-Dioxane	K₂CO₃	80	N.R.
4	Pd(PPh₃)₄	MTBE	K₂CO₃	80	Trace
5	Pd(PPh₃)₄	EtOAc	K₂CO₃	80	Trace
6	Pd(PPh₃)₄	DMSO	K₂CO₃	80	Trace
7	Pd(PPh₃)₄	DME	K₂CO₃	80	Trace
8	Pd(PPh₃)₄	DMF	K₂CO₃	80	76
9	Pd(PPh₃)₄	DMA	K₂CO₃	80	91
10	Pd(PPh₃)₄	DMA	K₃PO₄	80	64
11	Pd(PPh₃)₄	DMA	Cs₂CO₃	80	69
12	Pd(PPh₃)₄	DMA	Na₂CO₃	80	67
13	Pd(PPh₃)₄	DMA	t-BuONa	80	N.R.
14	Pd(dba)₂	DMA	K₂CO₃	80	61
15	Pd(PPh₃)₂Cl₂	DMA	K₂CO₃	80	77
16	PdBr₂	DMA	K₂CO₃	80	90
17	Pd(OAc)₂	DMA	K₂CO₃	80	91
18^b	Pd(OAc)₂	DMA	K₂CO₃	80	80
19	Pd(PPh₃)₄	DMA	K₂CO₃	100	87
20	Pd(PPh₃)₄	DMF	K₂CO₃	100	96

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