Magnetic Se/Fe/PCN-Catalyzed Oxidative Cracking Alkenes in O2

doi:10.6023/cjoc202201023

Abstract

Oxidative cracking reaction of alkenes is applied not only in the synthesis of carbonyl compounds, but also in biomass conversion and degradation of organic pollutants. It is an organic chemical reaction with potential industrial application value. Developing a suitable catalyst to promote the reaction using molecular oxygen as a cheap and safe oxidant under mild conditions is a meaningful research topic in the interdisciplinary field of organic chemistry and material chemistry. In this work, Se/Fe/PCN catalyst was designed and prepared. The experimental results showed that the material was of excellent catalytic activity for the oxidative cracking of styrene derivatives. Notably, the selectivity of the reaction is good, and the selectivity of aldehydes in the product could reach 70%~90%. The catalyst was magnetically separable, and could be reused for the next turn of reaction.

Key words: selenium, iron, oxidative cracking, alkene, carbonyl

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Wenjian Zhou, Xinrui Xiao, Yonghong Liu, Xu Zhang. Magnetic Se/Fe/PCN-Catalyzed Oxidative Cracking Alkenes in O₂[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1849-1855.

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Fig. & Tab. 7

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Entry	R or substrate	Conv.^b/%	Selectivity ^c/%
1	C₆H₅	83	2a: 85
2	4-FC₆H₄	90	2b: 88
3	2-ClC₆H₄	60	2c: 70
4	3-ClC₆H₄	79	2d: 80
5	4-ClC₆H₄	87	2e: 89
6	4-BrC₆H₄	83	2f: 87
7	4-CF₃C₆H₄	94	2g: 90
8	4-MeC₆H₄	90	2h: 85
9	3-MeC₆H₄	80	2i: 84
10	2-C₁₀H₇	63	2j: 75
11		70	2k: 78
12		81	2l: 85
13		72	2m: 76
14		79	2a: 88
15		72	2a: 90

Entry	R or substrate	Conv.^b/%	Selectivity ^c/%
1	C₆H₅	83	2a: 85
2	4-FC₆H₄	90	2b: 88
3	2-ClC₆H₄	60	2c: 70
4	3-ClC₆H₄	79	2d: 80
5	4-ClC₆H₄	87	2e: 89
6	4-BrC₆H₄	83	2f: 87
7	4-CF₃C₆H₄	94	2g: 90
8	4-MeC₆H₄	90	2h: 85
9	3-MeC₆H₄	80	2i: 84
10	2-C₁₀H₇	63	2j: 75
11		70	2k: 78
12		81	2l: 85
13		72	2m: 76
14		79	2a: 88
15		72	2a: 90

磁性Se/Fe/PCN催化烯烃在氧气中的氧化裂解反应

Magnetic Se/Fe/PCN-Catalyzed Oxidative Cracking Alkenes in O₂

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Entry	Solvent	t/h	Conversion^b/%	Selectivity^c/% of 2a
1	EtOAc	5	21	100
2	EtOAc	10	32	99
3	EtOAc	15	61	91
4	EtOAc	20	78	88
5	EtOAc	25	83	85
6	EtOAc	30	85	82
7	DMF	25	30	74
8	MeCN	25	55	65
9	DCM	25	28	70
10	1,4-Dioxane	25	24	78
11	Acetone	25	45	70

Entry	Oxidant	Cat.	Additive^b	Conv.^c/ %	Selectivity^d/ % of 2a
1	Air	Se/Fe/PCN	None	15	67
2	None (in N₂)	Se/Fe/PCN	None	0	0
3	O₂	Se/PCN	None	13	77
4	O₂	Fe/PCN	None	37	85
5	O₂	Se/Fe	None	9	65
6	O₂	Se/Fe/PCN	TEMPO (100%)	0	0
7	O₂	Se/Fe/PCN	Hydroquinone (100%)	0	0
8	O₂	Se/Fe/PCN	AIBN (100%)	97	90

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