Acid/Base-Co-catalyzed Formal Baeyer-Villiger Oxidation Reaction of Ketones: Using Molecular Oxygen as the Oxidant

被引:21
作者
Liu, Chun-Hua [1 ]
Wang, Zhuo [1 ]
Xiao, Li-Yun [1 ]
Mukadas [1 ]
Zhu, Dong-Sheng [1 ]
Zhao, Yu-Long [1 ]
机构
[1] Northeast Normal Univ, Fac Chem, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Jilin, Peoples R China
关键词
CARBON-CARBON BOND; AMINE HYDROCHLORIDE SALTS; HYDROGEN-PEROXIDE; H FUNCTIONALIZATION; EFFICIENT SYNTHESIS; 3-SUBSTITUTED CYCLOBUTANONES; ALPHA-DIAZOCARBONYLS; SYNTHETIC APPROACH; COUPLING REAGENTS; AMIDE SYNTHESIS;
D O I
10.1021/acs.orglett.8b02006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel acid/base-co-catalyzed formal Baeyer-Villiger oxidation of various ketones using O-2 as the sole oxidant under metal-free conditions has been developed for the first time. The reaction tolerates a wide range of ketones and anilines and provides a simple and efficient method for the construction of various amides and isoquinolin-1-ones from the reactions of ketones with anilines in a single step.
引用
收藏
页码:4862 / 4866
页数:5
相关论文
共 89 条
  • [1] Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity
    Alford, Joshua S.
    Abascal, Nadia C.
    Shugrue, Christopher R.
    Colvin, Sean M.
    Romney, David K.
    Miller, Scott J.
    [J]. ACS CENTRAL SCIENCE, 2016, 2 (10) : 733 - 739
  • [2] Aerobic Copper-Catalyzed Organic Reactions
    Allen, Scott E.
    Walvoord, Ryan R.
    Padilla-Salinas, Rosaura
    Kozlowski, Marisa C.
    [J]. CHEMICAL REVIEWS, 2013, 113 (08) : 6234 - 6458
  • [3] Halide-Promoted Dioxygenolysis of a Carbon-Carbon Bond by a Copper(II) Diketonate Complex
    Allpress, Caleb J.
    Milaczewska, Anna
    Borowski, Tomasz
    Bennett, Jami R.
    Tierney, David L.
    Arif, Atta M.
    Berreau, Lisa M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) : 7821 - 7824
  • [4] Regioselective Aliphatic Carbon-Carbon Bond Cleavage by a Model System of Relevance to Iron-Containing Acireductone Dioxygenase
    Allpress, Caleb J.
    Grubel, Katarzyna
    Szajna-Fuller, Ewa
    Arif, Atta M.
    Berreau, Lisa M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) : 659 - 668
  • [5] Baeyer A., 1899, BER DTSCH CHEM GES, V32, P3625, DOI DOI 10.1002/CBER.189903203151
  • [6] The Baeyer-Villiger oxidation of ketones with bis(trimethylsilyl) peroxide in the presence of ionic liquids as the solvent and catalyst
    Baj, Stefan
    Chrobok, Anna
    Slupska, Roksana
    [J]. GREEN CHEMISTRY, 2009, 11 (02) : 279 - 282
  • [7] ANODIC ALPHA-CLEAVAGE OF KETONES
    BECKER, JY
    MILLER, LL
    SIEGEL, TM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) : 849 - 853
  • [8] Converting phenylacetone monooxygenase into phenylcyclohexanone monooxygenase by rational design: Towards practical Baeyer-Villiger monooxygenases
    Bocola, M
    Schulz, F
    Leca, F
    Vogel, A
    Fraaije, MW
    Reetz, MT
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (7-8) : 979 - 986
  • [9] Copper-Catalyzed Cascade Cyclization Reactions of Isocyanides with α-Diazocarbonyls as N-Terminal Electrophiles: Efficient Synthesis of 2-Imidazolines and 1,1′-Biimidazoles
    Bu, Xiu-Bin
    Yu, Yang
    Li, Bin
    Zhang, Lu
    Chen, Jia-Jia
    Zhao, Yu-Long
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (02) : 351 - 356
  • [10] Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia
    Cao, Liping
    Ding, Jiaoyang
    Gao, Meng
    Wang, Zihua
    Li, Juan
    Wu, Anxin
    [J]. ORGANIC LETTERS, 2009, 11 (17) : 3810 - 3813