硒化银新材料催化的醇氧化反应

doi:10.6023/cjoc202011012

摘要/Abstract

通过在氮气中150 ℃下煅烧硒粉和银粉, 可以很方便地制备硒化银(Ag/Se)新材料. 该材料有着很强的氧运载能力, 可以活化分子氧, 从而实现催化氧化反应. 对该材料在醇氧化中的应用进行了研究, 为制备相关醛酮, 提供了一种清洁的新合成方法. 该方法适用于伯醇与仲醇的氧化反应, 并且对伯醇氧化有一定的选择性, 可以中等产率合成醛. 硒化银作为一种新颖的非均相硒催化材料, 未来有望获得更加广泛的应用, 从而显著推动硒催化化学的发展.

关键词: 硒, 银, 催化氧化, 醇, 羰基

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

引用此文

刘峰, 詹杰, 孙扬阳, 景崤壁. 硒化银新材料催化的醇氧化反应[J]. 有机化学, 2021, 41(5): 2099-2104.

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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参考文献 12

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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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