Sulfoximine Directed Intermolecular o-C-H Amidation of Arenes with Sulfonyl Azides

被引：163
|
作者：
Yadav, M. Ramu [1 ]
Rit, Raja K. [1 ]
Sahoo, Akhila K. [1 ]
机构：
[1] Univ Hyderabad, Sch Chem, Hyderabad 500134, Andhra Pradesh, India
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 07期
关键词：
CATALYZED DIRECT AMINATION; BOND FUNCTIONALIZATIONS; DIRECT ARYLATIONS; AZOLES; ACTIVATION; MECHANISM; ALKENYLATION; CHLOROAMINES; BENZOXAZOLES; INDOLES;
D O I：
10.1021/ol400411v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Ru(II)-catalyzed Intermolecular o-C-H amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method Is successfully employed for the synthesis of HMR 1766.
引用
收藏
页码：1638 / 1641
页数：4
相关论文
共 50 条
  • [1] Ruthenium-catalyzed 1,2,3-triazole directed intermolecular C-H amidation of arenes with sulfonyl azides
    Wang, Xiaoyu
    Zhang, Chen
    Li, Jue
    Jiang, Chong
    Su, Fu
    Zhan, Zhen
    Hai, Li
    Chen, Zhonghua
    Wu, Yong
    RSC ADVANCES, 2016, 6 (73) : 68929 - 68933
  • [2] Palladium-catalyzed intermolecular C–H amidation of indoles with sulfonyl azides
    Ziwei Hu
    Shuang Luo
    Qiang Zhu
    Science China(Chemistry), 2015, (08) : 1349 - 1353
  • [3] Palladium-catalyzed intermolecular C–H amidation of indoles with sulfonyl azides
    Ziwei Hu
    Shuang Luo
    Qiang Zhu
    Science China(Chemistry), 2015, 58 (08) : 1349 - 1353
  • [4] Palladium-catalyzed intermolecular C-H amidation of indoles with sulfonyl azides
    Ziwei Hu
    Shuang Luo
    Qiang Zhu
    Science China Chemistry, 2015, 58 : 1349 - 1353
  • [5] Palladium-catalyzed intermolecular C-H amidation of indoles with sulfonyl azides
    Hu, Ziwei
    Luo, Shuang
    Zhu, Qiang
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1349 - 1353
  • [6] Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C-H Bond Activation
    Kim, Ji Young
    Park, Sae Hume
    Ryu, Jaeyune
    Hwan, Seung Cho
    Kim, Seok Hwan
    Chang, Sukbok
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9110 - 9113
  • [7] Recent advances in metal directed C-H amidation/amination using sulfonyl azides and phosphoryl azides
    Rao, M. V. Krishna
    Kareem, Shaik
    Vali, Shaik Ramjan
    Reddy, B. V. Subba
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (42) : 8426 - 8462
  • [8] Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
    Bhanuchandra, M.
    Yadav, M. Ramu
    Rit, Raja K.
    Kuram, Malleswara Rao
    Sahoo, Akhila K.
    CHEMICAL COMMUNICATIONS, 2013, 49 (45) : 5225 - 5227
  • [9] Iridium(III)-Catalyzed Benzylic Amine Directed C-H Sulfonamidation of Arenes with Sulfonyl Azides
    Chen, Heng
    Huestis, Malcolm P.
    CHEMCATCHEM, 2015, 7 (05) : 743 - 746
  • [10] Transition metal catalysed intermolecular C-H amidation of arenes
    Kilaru, Praveen
    Das, Kushal
    Zhao, Pinjing
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
12345