Direct Acetoxylation of Arenes

Thi Anh Hong Nguyen; Duen Ren Hou

doi:10.1021/acs.orglett.1c02183

Direct Acetoxylation of Arenes

Thi Anh Hong Nguyen, Duen Ren Hou

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.

Original language	English
Pages (from-to)	8127-8131
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.1c02183
State	Published - 5 Nov 2021

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10.1021/acs.orglett.1c02183

Synthesis of Natural Products and Development of Aziridine-Related Methodology( II )
Hou, D.-R. (PI)
1/08/19 → 31/07/20
Project: Research
Synthesis of Natural Products and Development of Aziridine-Related Methodology(I)
Hou, D.-R. (PI)
1/08/18 → 31/07/19
Project: Research

Cite this

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abstract = "Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.",

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N2 - Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.

AB - Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.

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Direct Acetoxylation of Arenes

Abstract

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Projects

Synthesis of Natural Products and Development of Aziridine-Related Methodology( II )

Synthesis of Natural Products and Development of Aziridine-Related Methodology(I)

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