Direct Acetoxylation of Arenes.

Autor: Hong Nguyen TA; Department of Chemistry, National Central University, No. 300 Jhong-Da Road, Jhong-li, Taoyuan Taiwan 32001., Hou DR; Department of Chemistry, National Central University, No. 300 Jhong-Da Road, Jhong-li, Taoyuan Taiwan 32001.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2021 Nov 05; Vol. 23 (21), pp. 8127-8131. Date of Electronic Publication: 2021 Aug 03.
DOI: 10.1021/acs.orglett.1c02183
Abstrakt: 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 ( E ox , 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.
Databáze: MEDLINE