A facile aerobic copper-catalyzed α-oxygenation of aryl thioacetamides:: An efficient access to α-keto aryl Thioamides

被引：34
|
作者：
Moghaddam, Firouz Matloubi [1 ]
Mirjafary, Zohreh [1 ]
Saeidian, Hamdollah [1 ]
Javan, Marjan Jebeli [1 ]
机构：
[1] Sharif Univ Technol, Dept Chem, Lab Organ Synth & Nat Prod, Tehran, Iran
来源：
SYNLETT | 2008年 / 06期
关键词：
CuCl2 center dot 2H(2)O; oxygenation; alpha-keto aryl thioamides; thioacetomorpholides;
D O I：
10.1055/s-2008-1042925
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper(II) efficiently catalyzes the aerobic oxidation of aryl thioacetamides into the corresponding a-keto aryl thioamides in moderate to high yields in the presence of K2CO3 under O-2 atmosphere. This protocol is simple, clean, and generates water as the only byproduct. A mechanism is proposed for the reaction course.
引用
收藏
页码：892 / 896
页数：5
相关论文
共 50 条
  • [1] Copper-Catalyzed Synthesis of Aryl Thioamides from Aryl Aldehydes and Tetramethylthiuram Disulfide
    Zeng, Meng-Tian
    Wang, Min
    Peng, Han-Ying
    Cheng, Yu
    Dong, Zhi-Bing
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (03): : 644 - 650
  • [2] An Efficient Copper-Catalyzed Etherification of Aryl Halides
    Huang, Jinkun
    Chen, Ying
    Chan, Johann
    Ronk, Mike L.
    Larsen, Robert D.
    Faul, Margaret M.
    [J]. SYNLETT, 2011, (10) : 1419 - 1422
  • [3] Lithium pipecolinate as a facile and efficient ligand for copper-catalyzed hydroxylation of aryl halides in water
    Jing, Linhai
    Wei, Jiangtao
    Zhou, Li
    Huang, Zhiyong
    Li, Zhengkai
    Zhou, Xiangge
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4767 - 4769
  • [4] An efficient copper-catalyzed coupling of aryl halides with imidazoles
    Kiyomori, A
    Marcoux, JF
    Buchwald, SL
    [J]. TETRAHEDRON LETTERS, 1999, 40 (14) : 2657 - 2660
  • [5] Copper-catalyzed coupling of aryl iodides and tert-butyl β-keto esters: efficient access to α-aryl ketones and α-arylacetic acid tert-butyl esters
    Zhao, Duo
    Jiang, Yongwen
    Ma, Dawei
    [J]. TETRAHEDRON, 2014, 70 (20) : 3327 - 3332
  • [6] Copper-Catalyzed Cleavage of Aryl C(OH)-C Bonds to Access Aryl Nitriles
    Zheng, Yi
    Liu, Wenbo
    Ren, Yun-Lai
    Guo, Yinggang
    Tian, Xinzhe
    [J]. CHEMISTRYSELECT, 2021, 6 (47): : 13546 - 13550
  • [7] Copper-catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates: Synthesis of aryl/heteroaryl α-keto esters
    Saha, Pipas
    Ray, Sumit Kumar
    Singh, Vinod K.
    [J]. TETRAHEDRON LETTERS, 2017, 58 (18) : 1765 - 1769
  • [8] Efficient copper-catalyzed N-arylation of sulfoximines with aryl iodides and aryl bromides
    Sedelmeier, J
    Bolm, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6904 - 6906
  • [9] A Facile and Efficient Oxalyldihydrazide/Ketone-Promoted Copper-Catalyzed Amination of Aryl Halides in Water
    Zhu, Xinhai
    Su, Li
    Huang, Liye
    Chen, Gong
    Wang, Jinlong
    Song, Huacan
    Wanlal, Yiqian
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (05) : 635 - 642
  • [10] Towards a Practical and Efficient Copper-Catalyzed Trifluoromethylation of Aryl Halides
    Schareina, Thomas
    Wu, Xiao-Feng
    Zapf, Alexander
    Cotte, Alain
    Gotta, Matthias
    Beller, Matthias
    [J]. TOPICS IN CATALYSIS, 2012, 55 (7-10) : 426 - 431
12345