Catalytic Oxidation of Alcohols Using a 2,2,6,6-Tetramethylpiperidine-N-hydroxyammonium Cation

被引：19
|
作者：
Miller, Shelli A. [1 ]
Bisset, Kathryn A. [1 ]
Leadbeater, Nicholas E. [1 ]
Eddy, Nicholas A. [1 ]
机构：
[1] Univ Connecticut, Dept Chem, 55 North Eagleville Rd, Storrs, CT 06269 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 06期
关键词：
Oxidation; Hydroxyammonium salts; Synthetic methods; Alcohols; PENTAHYDRATE NAOCL-CENTER-DOT-5H(2)O CRYSTALS; ASYMMETRIC ALPHA-OXYAMINATION; TRIFLUOROMETHYL ALCOHOLS; OXOAMMONIUM CATIONS; NITROXYL RADICALS; ALDEHYDES; TEMPO; SALTS; MECHANISM; KETONES;
D O I：
10.1002/ejoc.201801718
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The oxidation of alcohols to aldehydes, ketones, and carboxylic acids is reported using 2,2,6,6-tetramethylpiperidine-4-acetamido-hydroxyammonium tetrafluoroborate as a catalyst in conjunction with sodium hypochlorite pentahydrate as a terminal oxidant. The reaction is generally complete within 30-120 min using an acetonitrile/water mix as the solvent, and no additives are required. Product yields are good to excellent and of particular note is that the methodology can be used to access aryl alpha-trifluoromethyl ketones.
引用
收藏
页码：1413 / 1417
页数：5
相关论文
共 50 条
  • [1] MECHANISM OF THE OXIDATION OF ALCOHOLS BY 2,2,6,6-TETRAMETHYLPIPERIDINE NITROSONIUM CATION
    SEMMELHACK, MF
    SCHMID, CR
    CORTES, DA
    TETRAHEDRON LETTERS, 1986, 27 (10) : 1119 - 1122
  • [2] The use of TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl) for the oxidation of primary and secondary alcohols.
    de Souza, MVN
    QUIMICA NOVA, 2004, 27 (02): : 287 - 292
  • [3] INFLUENCE OF 2,2,6,6-TETRAMETHYLPIPERIDINE AND OF 2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXIDE ON RADICALLY INDUCED STYRENE POLYMERIZATION
    HALLENSLEBEN, ML
    WIBOWO, TS
    WURM, H
    POLYMER BULLETIN, 1990, 24 (01) : 59 - 62
  • [4] Interaction of 2,2,6,6-tetramethylpiperidine-1-oxyl chloritewith alcohols
    I. M. Ganiev
    E. S. Suvorkina
    A. V. Igoshina
    N. N. Kabal"nova
    U. B. Imashev
    G. A. Tolstikov
    Russian Chemical Bulletin, 2002, 51 : 982 - 985
  • [5] Oxidation of glycerol by 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) in the presence of laccase
    Liebminger, Stefan
    Siebenhofer, Matthaeus
    Guebitz, Georg
    BIORESOURCE TECHNOLOGY, 2009, 100 (20) : 4541 - 4545
  • [6] Interaction of 2,2,6,6-tetramethylpiperidine-1-oxyl chlorite with alcohols
    Ganiev, IM
    Suvorkina, ES
    Igoshina, AV
    Kabal'nova, NN
    Imashev, UB
    Tolstikov, GA
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (06) : 982 - 985
  • [7] REACTION OF 2,2,6,6-TETRAMETHYLPIPERIDINE-NITROXIDE CATION WITH IRON IN ACETONITRILE
    IWAKURA, C
    TSUNAGA, M
    TAMURA, H
    ELECTROCHIMICA ACTA, 1974, 19 (09) : 593 - 595
  • [8] RECENT ADVANCES IN THE CATALYTIC-OXIDATION OF ALCOHOLS WITH 2,2,6,6-TETRAMETHYLPIPERIDINE-1-OXYL (TEMPO) AND ITS APPLICATION TO ORGANIC-SYNTHESIS
    INOKUCHI, T
    MATSUMOTO, S
    TORII, S
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1993, 51 (10) : 910 - 920
  • [9] STABILIZING ACTIVITY OF 2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL
    DULOG, L
    BLEHER, R
    MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1982, 3 (03): : 153 - 156
  • [10] Aerobic Oxidation of Benzylic Alcohols in Water by 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO)/Copper(II) 2-N-Arylpyrrolecarbaldimino Complexes
    Figiel, Pawel J.
    Sibaouih, Ahlam
    Ahmad, Jahir Uddin
    Nieger, Martin
    Raisanen, Minna T.
    Leskela, Markku
    Repo, Timo
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) : 2625 - 2632
12345