Visible Light Induced Oxidation of α-Diazo Esters for the Transition Metal-Free Synthesis of α-Keto Esters

doi:10.6023/cjoc202111020

Abstract

Herein, an aerobic oxidation approach for the synthesis of α-keto esters using oxygen as a cheap and pollution-free oxidant has been developed. By using readily available α-diazo esters as starting materials, the transformation was achieved by the inducement of visible light with eosin Y as the light sensitizer. The reactions proceed at room temperature under air atmosphere, tolerating substrates with broad scope, thus providing a green and facile synthetic approach to structurally diverse α-keto esters.

Key words: photocatalysis, transition metal-free, aerobic oxidation, α-diazo esters, α-keto esters

Cite this article

Baoli Zhao, Liangfeng Yang, Kai Cheng, Liyun Zhou, Jie-Ping Wan. Visible Light Induced Oxidation of α-Diazo Esters for the Transition Metal-Free Synthesis of α-Keto Esters[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4732-4737.

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Entry	Photocatalyst	Solvent	Light source	Yield^b/%
1	Rhodamine B	CH₃CN	Blue LED	68
2	—	CH₃CN	Blue LED	—
3	Rose Bengal	CH₃CN	Blue LED	33
4	Eosin Y	CH₃CN	Blue LED	83
5	Ru(bpy)₃Cl₂	CH₃CN	Blue LED	55
6	Ir(ppy)₃	CH₃CN	Blue LED	60
7	Eosin Y	CCl₄	Blue LED	39
8	Eosin Y	CH₂Cl₂	Blue LED	36
9	Eosin Y	THF	Blue LED	28
10	Eosin Y	DMF	Blue LED	61
11	Eosin Y	DMSO	Blue LED	52
12	Eosin Y	acetone	Blue LED	67
13	Eosin Y	CH₃CN	Green LED	50
14	Eosin Y	CH₃CN	household bulb	63
15	Eosin Y	CH₃CN	Red LED	37
16^c	Eosin Y	CH₃CN	Blue LED	81
17	Eosin Y	CH₃CN	dark	0

Entry	Photocatalyst	Solvent	Light source	Yield^b/%
1	Rhodamine B	CH₃CN	Blue LED	68
2	—	CH₃CN	Blue LED	—
3	Rose Bengal	CH₃CN	Blue LED	33
4	Eosin Y	CH₃CN	Blue LED	83
5	Ru(bpy)₃Cl₂	CH₃CN	Blue LED	55
6	Ir(ppy)₃	CH₃CN	Blue LED	60
7	Eosin Y	CCl₄	Blue LED	39
8	Eosin Y	CH₂Cl₂	Blue LED	36
9	Eosin Y	THF	Blue LED	28
10	Eosin Y	DMF	Blue LED	61
11	Eosin Y	DMSO	Blue LED	52
12	Eosin Y	acetone	Blue LED	67
13	Eosin Y	CH₃CN	Green LED	50
14	Eosin Y	CH₃CN	household bulb	63
15	Eosin Y	CH₃CN	Red LED	37
16^c	Eosin Y	CH₃CN	Blue LED	81
17	Eosin Y	CH₃CN	dark	0

无过渡金属条件下可见光诱导α-重氮酯的氧化合成α-酮酯