中国化学快报(英文版)2024,Vol.35Issue(2) :396-401.DOI:10.1016/j.cclet.2023.108660

Selective nickel-electrocatalyzed benzylic C-H oxygenation of functionalized alkyl arenes

Shunyao Tang Siyi Wang Dongmei Zhang Xinxing Zhang Guang Yang Yanwei Wang Youai Qiu
中国化学快报(英文版)2024,Vol.35Issue(2) :396-401.DOI:10.1016/j.cclet.2023.108660

Selective nickel-electrocatalyzed benzylic C-H oxygenation of functionalized alkyl arenes

Shunyao Tang 1Siyi Wang 1Dongmei Zhang 2Xinxing Zhang 2Guang Yang 1Yanwei Wang 1Youai Qiu1
扫码查看

作者信息

  • 1. State Key Laboratory of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China
  • 2. College of Chemistry,Key Laboratory of Advanced Energy Materials Chemistry(Ministry of Education),Renewable Energy Conversion and Storage Center(RECAST),Frontiers Science Center for New Organic Matter,Nankai University,Tianjin 300071,China
  • 折叠

Abstract

Herein,a site-selective paired electrochemical C-H oxidation of functionalized alkyl arenes promoted by nickel catalyst is disclosed.A Ni(ll)-dioxygen species formed in situ efficiently enable the oxidation pro-cess under mild conditions with a broad substrate scope with excellent functional group compatibilities,such as free carboxylic acid,aldehyde,halogen(including aryl iodide),amide and amino acid.The use of the nickel catalyst in combination with water provides a safe,green and economical method for oxidation of a range of molecules varying in complexity and drug derivatives,demonstrating its potential applica-tion in organic synthesis and the pharmaceutical industry.Reaction outcomes and mechanistic studies re-vealed the key role of the in situ Ni(Ⅱ)-dioxygen species for the subsequent oxidation of C(sp3)-H bonds,and short-lived reactive intermediates(aryl radical cation)was rapidly captured by the combination of a bipolar ultramicroelectrode(BUME)with nano-electrospray ionization mass spectrometry.

Key words

Electrochemical C-H oxidation/Functionalized alkyl arenes/Paired nickel-electrocatalysis/H2O oxidation/Ketones

引用本文复制引用

基金项目

国家重点研发计划(2022YFA1503200)

国家自然科学基金(22188101)

中央高校基本科研业务费专项(63223007)

Frontiers Science Center for New Organic Matter,Nankai University(63181206)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子:0.771
ISSN:1001-8417
参考文献量76
段落导航相关论文