Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes

doi:10.6023/cjoc202301016

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (8): 2953-2960.DOI: 10.6023/cjoc202301016 Previous Articles Next Articles

介孔ETS-10沸石担载Pd高效催化内炔氧化制备1,2-二酮

刘长俊^a, 胡慧玲^a, 刘宬宏^a, 朱超杰^b^,^*(), 唐天地^a^,^*()

a 常州大学石油化工学院江苏常州 213164
b 东南大学化学化工学院南京 211189

收稿日期:2023-01-17 修回日期:2023-03-03 发布日期:2023-03-30
基金资助:
国家自然科学基金(21776022); 国家自然科学基金(22178029)

Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes

Changjun Liu^a, Huiling Hu^a, Chenghong Liu^a, Chaojie Zhu^b(), Tiandi Tang^a()

a School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
b School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received:2023-01-17 Revised:2023-03-03 Published:2023-03-30
Contact: *E-mail: tangtiandi@cczu.edu.cn; 785001159@qq.com
Supported by:
The National Natural Science Foundation of China(21776022); The National Natural Science Foundation of China(22178029)

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Abstract

The 1,2-dione compounds was synthesized under clean reaction conditions over Pd/METS-10 catalyst. It has been found that the key step of the protocol is forming an electron donor-acceptor complex (EDX), as the coordination of Pd(II) and alkynyl. Then the nucleophilic addition and elimination reactions of dimethyl sulfoxide (DMSO) to the EDX were occurred, affording the target product. Pd/METS-10 catalyzed endo-acetylene oxidation possesses excellent product selectivity and good substrate scope. It is compatible with both symmetric and asymmetric endo-acetylene and is insensitive to the electronic properties and stereoscopic effects of the substrate. In addition, Pd/METS-10 catalyst showed excellent repetition performance in the reaction, with no significant loss of activity after five cycles. Finally, according to the characterization and control experiment results, the reaction mechanism of Pd/METS-10 catalyzed acetylene oxidation to produce 1,2-dione was proposed.

Key words: Pd/METS-10, internal alkyne, 1,2-diketone compound, electron donor-acceptor complex, oxidation reaction

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Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.

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Fig. & Tab. 9

Figure 1. Some important bioactive bases containing 1,2-di- ketone structural units

Scheme 1. Some protocols for synthesis of 1,2-dione com- pounds

Figure 2. XRD spectra (a), N2 adsorption-desorption curves (b), pore size distribution (c) of METS-10 and Pd/METS-10 samples, and XPS fitting spectrum of Pd/METS-10 sample (d)

Entry	Catalyst	Solvent	Temp./℃	Yield^b/%
1	None	DMSO	150	n.d.^c
2	METS-10	DMSO	150	n.d.
3	Pd(NO₃)₂^d	DMSO	150	41
4	Pd(OAc)₂^d	DMSO	150	37
5	Pd/METS-10	DMSO	150	92
6	Pd/METS-10	DMSO	150	91^e
7	Pd/METS-10	Benzene	150	n.d.
8	Pd/METS-10	Cycloethane	150	n.d.
9	Pd/METS-10	1,4-Dioxane	150	n.d.
10	Pd/METS-10	DMF	150	n.d.
11	Pd/METS-10	NMP	150	n.d.
12	Pd/METS-10	DMSO	130	57
13	Pd/METS-10	DMSO	110	30

Table 1. Reaction condition optimization

Table 2. Substrate scope of oxidation of internal alkynes

Table 3. Synthesis of quinoxalines from o-phenylenediamines and 1,2-diketones

Scheme 2. The control experiments of the oxidization of diphenylacetylene to 1,2-diketone

Scheme 3. Possible mechanism of Pd/ETS-10 catalyzed oxidation of 1,2-diaryl alkynes

Figure 3. Cyclic experiment of Pd/METS-10 catalyst in diphenylacetylene oxidation reaction

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介孔ETS-10沸石担载Pd高效催化内炔氧化制备1,2-二酮

Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes

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