TfOH-Catalyzed O—H Insertion of Carboxylic Acids with α-Aryl Diazoesters

doi:10.6023/cjoc202410026

Abstract

An efficient TfOH-catalyzed O—H insertion reaction of α-aryl diazoesters with carboxylic acids is reported. This metal-free protocol provides an operationally simple method for a one-pot assembly of diverse α-acyloxy esters in moderate to high yields with a broad substrate scope. All starting materials are readily available, and the reactions can be conducted in the open air at room temperature.

Key words: carboxylic acids, α-aryl diazoesters, TfOH, O—H insertion

Cite this article

Guifang Chen, Hongqiang Li, Xingrong Zeng. TfOH-Catalyzed O—H Insertion of Carboxylic Acids with α-Aryl Diazoesters[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2537-2544.

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Entry	Catalyst	Solvent	Yield^b/%
1	Tf₂NH	CH₂Cl₂	—
2	TfOH	CH₂Cl₂	60
3	TsOH•H₂O	CH₂Cl₂	—
4	TFA	CH₂Cl₂	—
5	TfOH	DCE	64
6	TfOH	CHCl₃	50
7	TfOH	THF	—
8	TfOH	MeCN	13
9	TfOH	Dioxane	32
10^c	TfOH	DCE	29
11^c,d	TfOH	DCE	45
12^c,d	TfOH	DCE	59^e/69^g/80^h/76ⁱ
13^c,d	TfOH	DCE	50^e,f
14^c,d	TfOH	DCE	45^j/63^k

Entry	Catalyst	Solvent	Yield^b/%
1	Tf₂NH	CH₂Cl₂	—
2	TfOH	CH₂Cl₂	60
3	TsOH•H₂O	CH₂Cl₂	—
4	TFA	CH₂Cl₂	—
5	TfOH	DCE	64
6	TfOH	CHCl₃	50
7	TfOH	THF	—
8	TfOH	MeCN	13
9	TfOH	Dioxane	32
10^c	TfOH	DCE	29
11^c,d	TfOH	DCE	45
12^c,d	TfOH	DCE	59^e/69^g/80^h/76ⁱ
13^c,d	TfOH	DCE	50^e,f
14^c,d	TfOH	DCE	45^j/63^k

TfOH催化羧酸与α-芳基重氮酯的O—H插入反应