Silver Selenide as the Novel Catalytic Material for Alcohol Oxidation

doi:10.6023/cjoc202011012

Abstract

By calcining selenium powder and silver powder at 150 ℃ under N₂ protection, the novel material silver selenide (Ag/Se) could be easily fabricated. It possessed very strong oxygen carrier features and could activate the molecular oxygen to achieve the catalytic oxidation reactions. In this work, the Ag/Se-catalyzed alcohol oxidation reactions were investigated to afford a novel clean method for the synthesis of carbonyls. It could be applied for the oxidation reactions of primary and secondary alcohols, and could catalyze the selective oxidation of primary alcohols to synthesize aldehydes in moderate yields. Ag/Se as the novel Se-containing catalytic material may be comprehensively applied in future and significantly pushes forward the development of the chemistry of Se catalysis.

Key words: selenium, silver, catalyzed oxidation, alcohol, carbonyl

Cite this article

Feng Liu, Jie Zhan, Yangyang Sun, Xiaobi Jing. Silver Selenide as the Novel Catalytic Material for Alcohol Oxidation[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2099-2104.

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Entry	R¹	R²	2a	Yield^b/%
1	Ph,	Ph	2a	85, 82^c, 84^c
2	4-MeC₆H₄,	4-MeC₆H₄	2b	88
3	4-MeOC₆H₄,	4-MeOC₆H₄	2c	91
4	4-FC₆H₄,	4-FC₆H₄	2d	72
5	4-ClC₆H₄,	4-ClC₆H₄	2e	77
6	2-ClC₆H₄,	Ph	2f	79
7	Ph,	Me	2g	67 (89)
8	4-MeC₆H₄	Me	2h	84
9	4-MeOC₆H₄	Me	2i	87
10	4-NO₂C₆H₄	Me	2j	73
11	4-NCC₆H₄	Me	2k	75
12	3-ClC₆H₄	Me	2l	74
13			2m	68
14			2n	(73)
15	n-C₅H₁₁	Me	2o	(75)
16	Ph	H	2p	56
17	4-MeC₆H₄	H	2q	50
18	4-ClC₆H₄	H	2r	62
19	n-C₅H₁₁	H	2s	(65)

Entry	R¹	R²	2a	Yield^b/%
1	Ph,	Ph	2a	85, 82^c, 84^c
2	4-MeC₆H₄,	4-MeC₆H₄	2b	88
3	4-MeOC₆H₄,	4-MeOC₆H₄	2c	91
4	4-FC₆H₄,	4-FC₆H₄	2d	72
5	4-ClC₆H₄,	4-ClC₆H₄	2e	77
6	2-ClC₆H₄,	Ph	2f	79
7	Ph,	Me	2g	67 (89)
8	4-MeC₆H₄	Me	2h	84
9	4-MeOC₆H₄	Me	2i	87
10	4-NO₂C₆H₄	Me	2j	73
11	4-NCC₆H₄	Me	2k	75
12	3-ClC₆H₄	Me	2l	74
13			2m	68
14			2n	(73)
15	n-C₅H₁₁	Me	2o	(75)
16	Ph	H	2p	56
17	4-MeC₆H₄	H	2q	50
18	4-ClC₆H₄	H	2r	62
19	n-C₅H₁₁	H	2s	(65)

Entry	Oxidant	Cat.	Additive^b	Yield^c/%
1	Air	Ag/Se	None	67
2	H₂O₂ (in N₂)	Ag/Se	None	82
3	None (in N₂)	Ag/Se	None	0
4	O₂	Ag	None	37
5	O₂	AgNO₃	None	28
6	O₂	Se	None	0
7	O₂	Ag₂Se	None	72
8	O₂	Ag/Se	TEMPO (100%)	12
9	O₂	Ag/Se	Hydroquinone (100%)	5
10	H₂O₂ (in N₂)	Ag/Se	TEMPO (100%)	62
11	H₂O₂ (in N₂)	Ag/Se	Hydroquinone (100%)	47

Entry	Oxidant	Cat.	Additive^b	Yield^c/%
1	Air	Ag/Se	None	67
2	H₂O₂ (in N₂)	Ag/Se	None	82
3	None (in N₂)	Ag/Se	None	0
4	O₂	Ag	None	37
5	O₂	AgNO₃	None	28
6	O₂	Se	None	0
7	O₂	Ag₂Se	None	72
8	O₂	Ag/Se	TEMPO (100%)	12
9	O₂	Ag/Se	Hydroquinone (100%)	5
10	H₂O₂ (in N₂)	Ag/Se	TEMPO (100%)	62
11	H₂O₂ (in N₂)	Ag/Se	Hydroquinone (100%)	47

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