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Selective Oxidative Cleavage of the C-C Bond in α,β-Epoxy Ketone into Carbonyl Compounds.

ABSTRACT: This method afforded aromatic carbonyl compounds under TBHP via selective oxidative cleavage of the C-C bond in α,β-epoxy ketones. Aromatic acid came from the aroyl section, and aromatic aldehyde came from the other aromatic group. TBHP acted as a free radical initiator and oxidant. The reaction within the solvent went through a ring-opening addition, cleavage of the C-C bond in the ethylene oxide section, and oxidation, affording the target compounds in moderate to good yields. The HPLC yield of aromatic aldehyde was up to 91%. The HPLC yield of aromatic acid was up to 99%. The reaction under solvent-free conditions gave two kinds of aromatic acids coming from different moieties of α,β-epoxy ketone via the further oxidation of aromatic aldehyde. The substituent effect was discussed, and the reaction mechanism was proposed. This method allowed the reaction to occur in a simple system metal-free.

SUBMITTER: Jiang B

PROVIDER: S-EPMC9245109 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Selective Oxidative Cleavage of the C-C Bond in α,β-Epoxy Ketone into Carbonyl Compounds.

Jiang Bing B Li Huai-Zhu HZ Li Rui-Jun RJ Zhang Jianye J Zhang Yun-Xiao YX

ACS omega 20220610 25

This method afforded aromatic carbonyl compounds under TBHP via selective oxidative cleavage of the C-C bond in α,β-epoxy ketones. Aromatic acid came from the aroyl section, and aromatic aldehyde came from the other aromatic group. TBHP acted as a free radical initiator and oxidant. The reaction within the solvent went through a ring-opening addition, cleavage of the C-C bond in the ethylene oxide section, and oxidation, affording the target compounds in moderate to good yields. The HPLC yield o ...[more]

PMID: 35785280

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