An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions

doi:10.6023/cjoc201904069

Abstract

A simple and highly efficient palladium nanoparticles catalytic system was applied in Suzuki coupling reaction. This system could catalyze a variety of aryl halide and arylboronic acid substrates with a wide range of functional groups. A high turnover number of 90000 was obtained with the catalyst loading as low as 0.001 mol%. This catalyst system exhibited good stability and longevity.

Key words: aryl hailde, arylboronic acid, palladium nanoparticle, Suzuki coupling

Cite this article

Li Hengchao, Zhao Ling, Liu Yan, Zhang Xia, Li Wangbing, Jing Linhai, Huang Jin, Wang Wei. An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3207-3214.

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Fig. & Tab. 6

Scheme 1. Pd/tetraphosphine-catalyzed Suzuki coupling reaction of aryl halides

Scheme 2. Application of palladium nanoparticles catalytic system in organic synthesis


Entry	Base	Solvent	TBAB/mmol	Time/h	Yield^b/%
1	Et₃N	DMA	0.375	8	0
2	NaOAc	DMA	0.375	8	0
3	NaHCO₃	DMA	0.375	8	10
4	Na₂CO₃	DMA	0.375	8	17
5	K₂CO₃	DMA	0.375	8	100
6	K₃PO₄	DMA	0.375	8	88
7	NaOH	DMA	0.375	8	19
8	K₂CO₃	DMA	0.375	2	96
9	K₂CO₃	DMF	0.375	2	100
10	K₂CO₃	1, 4-Dioxane	0.375	2	58
11	K₂CO₃	n-Butanol	0.375	2	26
12	K₂CO₃	Toluene	0.375	2	63
13	K₂CO₃	DMF	0.125	1	94
14	K₂CO₃	DMF	0.25	1	85
15	K₂CO₃	DMF	0.375	1	79
16	K₂CO₃	DMF	0.5	1	84

Table 1. Optimization of reaction conditions

Figure 1. Conversion vs. time plot for Suzuki reactionReaction conditions: 1a (0.5 mmol), 2a (1.0 mmol), [Pd(C3H5)Cl]2 (0.0005 mmol), K2CO3 (1.0 mmol), DMF (1.0 mL), TBAB (0.125 mmol), under argon, 100 ℃). (■) Control experiment; (○) Hg(0) (0.5 mmol) poisoning experiment

Table 2. Suzuki coupling of 4-nitrochlorobenzene with arylboronic acids

Table 3. Suzuki coupling of aryl halides with phenylboronic acid

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基于简单高效钯纳米粒子催化Suzuki偶联反应的研究