Phenazinium Salt-Catalyzed Aerobic Oxidative Amidation of Aromatic Aldehydes

被引:97
|
作者
Leow, Dasheng [1 ,2 ]
机构
[1] Inst Bioengn & Nanotechnol, Singapore 138669, Singapore
[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
AMIDE BOND FORMATION; LIGHT PHOTOREDOX CATALYSIS; 5-METHYLPHENAZINIUM SALTS; SUCCINIC DEHYDROGENASE; AQUEOUS-SOLUTION; AMINES; PHOTOCHEMISTRY; ESTERIFICATION; ALCOHOLS; PEPTIDE;
D O I
10.1021/ol5029354
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amides are prevalent in organic synthesis. Developing an efficient synthesis that avoids expensive oxidants and heating is highly desirable. Here the oxidative amidation of aromatic aldehydes is reported using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, at low catalytic loading (1-2 mol %). The reaction proceeds at ambient temperature and uses air as the sole oxidant. The operationally easy procedure provides an economical, green, and mild alternative for the formation of amide bonds.
引用
收藏
页码:5812 / 5815
页数:4
相关论文
共 50 条
  • [1] Nickel salt-catalyzed addition reaction of arylboronic acids to aromatic aldehydes
    Zhou, Li
    Du, Xin
    He, Ren
    Ci, Zhenhua
    Bao, Ming
    TETRAHEDRON LETTERS, 2009, 50 (04) : 406 - 408
  • [2] Nickel-catalyzed oxidative esterification and amidation of aldehydes
    Whittaker, Aaron M.
    George, David T.
    Dong, Vy M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [3] Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes
    Jiang, Biao-Lin
    Xu, Bao-Hua
    Wang, Meng-Liang
    Li, Zeng-Xi
    Liu, Dian-Sheng
    Zhang, Suo-Jiang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (05) : 977 - 983
  • [4] Cu(Ⅱ)-catalyzed aerobic oxidative amidation of azoarenes with amides
    Gang Li
    Xiaoting Chen
    Xulu Lv
    Chunqi Jia
    Panpan Gao
    Ya Wang
    Suling Yang
    Science China(Chemistry), 2018, 61 (06) : 660 - 663
  • [5] Cu(Ⅱ)-catalyzed aerobic oxidative amidation of azoarenes with amides
    Gang Li
    Xiaoting Chen
    Xulu Lv
    Chunqi Jia
    Panpan Gao
    Ya Wang
    Suling Yang
    Science China(Chemistry), 2018, (06) : 660 - 663
  • [6] Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols
    Luo, Xin-Long
    Ge, Danhua
    Yu, Zi-Lun
    Chu, Xue-Qiang
    Xu, Pei
    RSC ADVANCES, 2021, 11 (49) : 30937 - 30942
  • [7] Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Aldehydes
    Li, Yuanming
    Jia, Fan
    Li, Zhiping
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (01) : 82 - 86
  • [8] Aerobic Oxidative Amidation of Aromatic and Cinnamic Aldehydes with Secondary Amines by CuI/2-Pyridonate Catalytic System
    Zhu, Mingwen
    Fujita, Ken-ichi
    Yamaguchi, Ryohei
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9102 - 9109
  • [9] Pd-catalyzed oxidative amidation of aldehydes with hydrogen peroxide
    Suto, Yutaka
    Yamagiwa, Noriyuki
    Torisawa, Yasuhiro
    TETRAHEDRON LETTERS, 2008, 49 (40) : 5732 - 5735
  • [10] Oxidative Amidation of Aromatic Ethers Catalyzed by Rhodium Acetate
    Deng, Yu-Xing
    Xie, Jiang-Ping
    Zhang, Wen-Wen
    Yin, Ping
    Yu, Jing
    He, Ling
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (04) : 1077 - 1082