Pd(II)-catalyzed decarboxylative acylation of phenylacetamides with α-oxocarboxylic acids via C-H bond activation

被引:115
|
作者
Park, Jihye [1 ]
Kim, Minyoung [1 ]
Sharma, Satyasheel [1 ]
Park, Eonjeong [1 ]
Kim, Aejin [1 ]
Lee, Sang Hwi [1 ]
Kwak, Jong Hwan [1 ]
Jung, Young Hoon [1 ]
Kim, In Su [1 ]
机构
[1] Sungkyunkwan Univ, Sch Pharm, Suwon 440746, South Korea
基金
新加坡国家研究基金会;
关键词
OXIDATIVE ORTHO-ACYLATION; TERT-BUTYL HYDROPEROXIDE; O-METHYL OXIMES; SIMPLE ARENES; PALLADIUM COMPLEXES; ROOM-TEMPERATURE; ALDEHYDES; ACETANILIDES; DERIVATIVES; BENZAMIDES;
D O I
10.1039/c3cc38764j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed decarboxylative acylation of phenylacetamides with alpha-oxocarboxylic acids via C-H bond activation is described. This protocol provides efficient access to a range of ortho-acyl phenylacetamides, which can be easily converted to 3-isochromanone derivatives.
引用
收藏
页码:1654 / 1656
页数:3
相关论文
共 50 条
  • [1] PD(II)-CATALYZED DECARBOXYLATIVE ACYLATION OF PHENYLACETAMIDES WITH A-OXOCARBOXYLIC ACIDS VIA C-H BOND ACTIVATION AND APPLICATION TO THE SYNTHESIS OF 3-ISOCHROMANONE
    Park, Jihye
    Kim, Mirim
    Kim, Minyoung
    Kim, In Su
    [J]. DRUG METABOLISM REVIEWS, 2014, 45 : 106 - 107
  • [2] Decarboxylative Acylation of Arenes with α-Oxocarboxylic Acids via Palladium-Catalyzed C-H Activation
    Li, Mingzong
    Ge, Haibo
    [J]. ORGANIC LETTERS, 2010, 12 (15) : 3464 - 3467
  • [3] Cu(II)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides
    Li, Dengke
    Wang, Min
    Liu, Jie
    Zhao, Qiong
    Wang, Lei
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (35) : 3640 - 3642
  • [4] Decarboxylative Acylation of Cyclic Enamides with α-Oxocarboxylic Acids by Palladium-Catalyzed C-H Activation at Room Temperature
    Wang, Hua
    Guo, Li-Na
    Duan, Xin-Hua
    [J]. ORGANIC LETTERS, 2012, 14 (17) : 4358 - 4361
  • [5] Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C-H bond activation
    Gong, Wei-Jie
    Liu, De-Xian
    Li, Fei-Long
    Gao, Jun
    Li, Hong-Xi
    Lang, Jian-Ping
    [J]. TETRAHEDRON, 2015, 71 (08) : 1269 - 1275
  • [6] Unprecedented ortho-acylation of azoxybenzenes with α-oxocarboxylic acids by Pd-catalyzed C-H activation and decarboxylation
    Li, Hongji
    Li, Pinhua
    Zhao, Qiong
    Wang, Lei
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (80) : 9170 - 9172
  • [7] C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation
    Chen, Xiaopei
    Cui, Xiuling
    Wu, Yangjie
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3722 - 3725
  • [8] Theoretical studies on the mechanism of Pd2+-catalyzed regioselective C-H acylation of azoxybenzenes with α-oxocarboxylic acids
    Hu, Po
    Wang, Shaowei
    Wang, YouJia
    Deng, Chao
    Zhang, Weihua
    [J]. DALTON TRANSACTIONS, 2018, 47 (41) : 14644 - 14651
  • [9] Pd-catalyzed oxidative acylation of 2-phenoxypyridines with alcohols via C-H bond activation
    Kim, Minyoung
    Sharma, Satyasheel
    Park, Jihye
    Kim, Mirim
    Choi, Yeonhee
    Jeon, Yukyoung
    Kwak, Jong Hwan
    Kim, In Su
    [J]. TETRAHEDRON, 2013, 69 (32) : 6552 - 6559
  • [10] Palladium-catalyzed decarboxylative C2-acylation of indoles with α-oxocarboxylic acids
    Pan, Changduo
    Jin, Hongming
    Liu, Xu
    Cheng, Yixiang
    Zhu, Chengjian
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (28) : 2933 - 2935