Mechanistic studies on Cu(NO3)2/TEMPO-catalyzed aerobic oxidation of alcohols to carboxylic acids

被引:1
|
作者
Yu, Yibo [1 ]
Sun, Zhao [2 ]
Guo, Yin-Long [2 ]
Zhang, Xue [2 ]
Qian, Hui [1 ]
Ma, Shengming [1 ,2 ]
机构
[1] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, 220 Handan Lu, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 18期
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
BENZYLIC ALCOHOLS; COPPER(II); ALDEHYDES;
D O I
10.1039/d4qo00791c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidation of alcohols to carbonyl compounds is one of the most important and fundamental reactions in organic chemistry. Such aerobic reactions that provide aldehydes or ketones mediated by copper and nitroxyl have been well developed during the past several decades. Recently, we successfully realized the aerobic oxidation of primary alcohols to carboxylic acids catalyzed by Cu/TEMPO for the first time. Herein, a mechanism involving a Cu(NO3)(2)-TEMPO adduct as identified by SAESI-MS studies is proposed, which is supported by our experimental studies and density functional theory (DFT) calculations.
引用
收藏
页码:5003 / 5009
页数:7
相关论文
共 50 条
  • [31] SIMPLIFIED PROCEDURE FOR TEMPO-CATALYZED OXIDATION: SELECTIVE OXIDATION OF ALCOHOLS, α-HYDROXY ESTERS, AND AMIDES USING TEMPO AND CALCIUM HYPOCHLORITE
    Reddy, Sabbasani Rajasekhara
    Stella, Selvaraj
    Chadha, Anju
    SYNTHETIC COMMUNICATIONS, 2012, 42 (23) : 3493 - 3503
  • [32] Copper on charcoal: TEMPO free Cu0 nanoparticles catalyzed aerobic oxidation of alcohols
    Wang, Zhiwei
    Zhao, Rong
    Lin, Jia
    Liu, Chaoyang
    Jia, Qiang
    Chu, Changhu
    TETRAHEDRON, 2024, 151
  • [33] Cu-Catalyzed Aerobic Oxidation of Alcohols with a Multi-Functional NMI-TEMPO
    Wang, Lianyue
    Bie, Zhixing
    Shang, Sensen
    Li, Guosong
    Niu, Jingyang
    Gao, Shuang
    CHEMISTRYSELECT, 2018, 3 (12): : 3386 - 3390
  • [34] Selective aerobic oxidation of benzylic and allylic alcohols catalyzed by Cu(OAc)2/TEMPO/Et2NH
    Pasupuleti, Bala Gangadhar
    Gogoi, Achinta
    Bez, Ghanashyam
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2021, 60 (04): : 589 - 597
  • [35] Catalytic conversion of a lignin model compound to value-added products using Cu/TEMPO-catalyzed aerobic oxidation
    Lin, Jia-Yin
    Lin, Kun-Yi Andrew
    BIOMASS CONVERSION AND BIOREFINERY, 2019, 9 (03) : 617 - 623
  • [36] Aerobic copper/TEMPO-catalyzed oxidation of primary alcohols to aldehydes using a microbubble strategy to increase gas concentration in liquid phase reactions
    Mase, Nobuyuki
    Mizumori, Tomoya
    Tatemoto, Yuji
    CHEMICAL COMMUNICATIONS, 2011, 47 (07) : 2086 - 2088
  • [37] Copper/TEMPO-catalyzed continuous aerobic alcohol oxidation in a micro-packed bed reactor
    Zhang, Chenghao
    Duan, Xiaonan
    Yin, Jiabin
    Lou, Fengyan
    Zhang, Jisong
    REACTION CHEMISTRY & ENGINEERING, 2022, 7 (06) : 1289 - 1296
  • [38] Selective iron-catalyzed aerobic oxidation of alcohols in water to carboxylic acids mediated by additives
    Yu, Han
    Ren, Jingjing
    Xie, Ya
    Su, Xiaofang
    Wang, Aiping
    Yan, Likai
    Jiang, Feng
    Wei, Yongge
    GREEN CHEMISTRY, 2022, 24 (17) : 6511 - 6516
  • [39] A TEMPO-Free Copper-Catalyzed Aerobic Oxidation of Alcohols
    Xu, Boran
    Lumb, Jean-Philip
    Arndtsen, Bruce A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (14) : 4208 - 4211
  • [40] Aerobic Oxidation of Propargylic Alcohols to α,β-Unsaturated Alkynals or Alkynones Catalyzed by Fe(NO3)3•9H2O, TEMPO and Sodium Chloride in Toluene
    Liu, Jinxian
    Xie, Xi
    Ma, Shengming
    SYNTHESIS-STUTTGART, 2012, 44 (10): : 1569 - 1576