Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion

Jiefan Gu; Yuting Wan; Hongfei Ma; Hongjun Zhu; Hongzhong Bu; Ying'ao Zhou; Weijian Zhang; Zheng Guang Wu; Yufeng Li

doi:10.1016/j.tet.2021.132298

Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion

Jiefan Gu, Yuting Wan, Hongfei Ma, Hongjun Zhu, Hongzhong Bu, Ying'ao Zhou, Weijian Zhang, Zheng Guang Wu, Yufeng Li

School of Chemistry and Moleculai Engineering

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

10 Scopus citations

Abstract

A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.

Original language	English
Article number	132298
Journal	Tetrahedron
Volume	93
DOIs	https://doi.org/10.1016/j.tet.2021.132298
State	Published - 30 Jul 2021

Keywords

Benzylic C–H bond
Carbonyl compound
Ferric sulfate catalysis
High selectivity
Photo-oxidation

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10.1016/j.tet.2021.132298

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title = "Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion",

abstract = "A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.",

keywords = "Benzylic C–H bond, Carbonyl compound, Ferric sulfate catalysis, High selectivity, Photo-oxidation",

author = "Jiefan Gu and Yuting Wan and Hongfei Ma and Hongjun Zhu and Hongzhong Bu and Ying'ao Zhou and Weijian Zhang and Wu, {Zheng Guang} and Yufeng Li",

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year = "2021",

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doi = "10.1016/j.tet.2021.132298",

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TY - JOUR

T1 - Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion

AU - Gu, Jiefan

AU - Wan, Yuting

AU - Ma, Hongfei

AU - Zhu, Hongjun

AU - Bu, Hongzhong

AU - Zhou, Ying'ao

AU - Zhang, Weijian

AU - Wu, Zheng Guang

AU - Li, Yufeng

PY - 2021/7/30

Y1 - 2021/7/30

N2 - A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.

AB - A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.

KW - Benzylic C–H bond

KW - Carbonyl compound

KW - Ferric sulfate catalysis

KW - High selectivity

KW - Photo-oxidation

UR - http://www.scopus.com/inward/record.url?scp=85109687071&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2021.132298

DO - 10.1016/j.tet.2021.132298

M3 - 文章

AN - SCOPUS:85109687071

SN - 0040-4020

VL - 93

JO - Tetrahedron

JF - Tetrahedron

M1 - 132298

ER -

Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion

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Keywords

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