Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction

doi:10.6023/cjoc202112014

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1792-1798.DOI: 10.6023/cjoc202112014 Previous Articles Next Articles

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酸性沸石HBeta催化的傅克烯基化反应

刘会丽^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:2021-12-06 修回日期:2022-01-12 发布日期:2022-02-25
通讯作者: 朱超杰, 唐天地
基金资助:
国家自然科学基金(21776022); 国家自然科学基金(22178029)

Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction

Huili 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:2021-12-06 Revised:2022-01-12 Published:2022-02-25
Contact: Chaojie Zhu, Tiandi Tang
Supported by:
National Natural Science Foundation of China(21776022); National Natural Science Foundation of China(22178029)

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Abstract

The Friedel-Crafts alkenylation of various alkynes and electron-rich arenes was achieved under mild conditions by using acidic zeolite Hbeta as catalyst. HBeta possesses Lewis acid sites (LAS) and Bronsted acid sites (BAS), which are adsorption activation sites and protonation sites for alkynes, respectively. Preliminary studies have shown that the reaction proceeds through a BAS-promoted alkenyl cation process. The strong interaction between the alkenyl cation and BAS prevents the highly reactive alkenyl cation from polymerizing, avoiding the formation of oligomerized by-products. HBeta, as a heterogeneous catalyst, showed excellent reproducibility in the alkyne alkenylation reaction and could be recycled at least 5 times without significant loss of activity. Finally, according to the experimental results, the reaction mechanism of HBeta-catalyzed alkyne alkenylation was proposed.

Key words: HBeta zeollite, alkyne, Friedel-Crafts alkenylation reaction, alkenyl cation

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Huili Liu, Chaojie Zhu, Tiandi Tang. Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1792-1798.

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Fig. & Tab. 5

Scheme 1. Reaction mechanism of alkynes hydroarylation

Figure 1. XRD spectra (a), N2 adsorption-desorption curves (b), pore size distribution (c) and NH3-TPD curves (d) of Beta and HBeta samples

Entry	Catalyst	Temp./℃	Time/h	GC yield/%
1	Beta	r.t.^b	3	n.d.^c
2	HBeta	r.t.	3	n.d.
3	Beta	60	3	4
4	HBeta	60	3	31
5	Beta	100	3	35
6	HBeta	100	3	81
7	Beta	100	4	57
8	HBeta	100	4	>99

Table 1. Reaction condition optimization

Scheme 2. Control experiments and KIE experiment of alkenylation reaction

Scheme 3. Reaction mechanism of alkynes hydroarylation catalyzed by HBeta zeolite

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酸性沸石HBeta催化的傅克烯基化反应

Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction

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