Cobalt(II)-Catalyzed Oxidative C-H Alkenylations: Regio- and Site-Selective Access to Isoindolin-1-one

被引:154
|
作者
Ma, Wenbo [1 ]
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源
ACS CATALYSIS | 2015年 / 5卷 / 05期
基金
欧洲研究理事会;
关键词
C-H activation; alkenylation; cobalt; mechanism; oxidative annulation; CATALYZED DIRECT ARYLATION; BOND FORMATION; CARBON-HYDROGEN; HG2+ IONS; COBALT; PALLADIUM; ALKYNES; HYDROARYLATION; FUNCTIONALIZATIONS; FLUORESCENT;
D O I
10.1021/acscatal.5b00322
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Isoindolinone derivatives were prepared in a step-economical fashion by a C-H/N-H functionalization process with a catalytic system composed of Co(OAc)(2) and Mn(OAc)(2) or AgOPiv. The oxidative annulation by benzamides occurred efficiently with differently substituted electron-deficient alkenes. Mechanistic studies were indicative of a kinetically relevant, carboxylate-assisted C-H cobaltation.
引用
收藏
页码:2822 / 2825
页数:4
相关论文
共 50 条
  • [1] Ruthenium-catalyzed regio- and site-selective ortho C-H borylation of phenol derivatives
    Homma, Yuki
    Fukuda, Kazuishi
    Iwasawa, Nobuharu
    Takaya, Jun
    CHEMICAL COMMUNICATIONS, 2020, 56 (73) : 10710 - 10713
  • [2] Rhodium(III)-Catalyzed C-H Functionalization in Water for Isoindolin-1-one Synthesis
    Wu, Shangze
    Wu, Xiaoyan
    Fu, Chunling
    Ma, Shengming
    ORGANIC LETTERS, 2018, 20 (10) : 2831 - 2834
  • [3] Cobalt(iii)-catalyzed site-selective C-H amidation of pyridones and isoquinolones
    Gao, Feng
    Han, Xu
    Li, Chunpu
    Liu, Lingjun
    Cong, Zhanqing
    Liu, Hong
    RSC ADVANCES, 2018, 8 (57): : 32659 - 32663
  • [4] Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Cyclobutanes
    Garlets, Zachary J.
    Wertz, Benjamin D.
    Liu, Wenbin
    Voight, Eric A.
    Davies, Huw M. L.
    CHEM, 2020, 6 (01): : 304 - 313
  • [5] Rh(III) and Ru(II)-Catalyzed Site-Selective C-H Alkynylation of Quinolones
    Kang, Dahye
    Hong, Sungwoo
    ORGANIC LETTERS, 2015, 17 (08) : 1938 - 1941
  • [6] Cobalt(III)-Catalyzed C-H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton
    Scamp, Ryan J.
    DeRamon, Edward
    Paulson, Eric K.
    Miller, Scott J.
    Ellman, Jonathan A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (02) : 890 - 895
  • [7] Palladium(ii) catalyzed site-selective C-H olefination of imidazo[1,2-a]pyridines
    Tali, Javeed Ahmad
    Kumar, Gulshan
    Singh, Davinder
    Shankar, Ravi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (43) : 9401 - 9406
  • [8] Electrochemical oxidative C-H sulfonylation of thiophenes: Site-selective access to 2-arylsulfonylthiophenes
    Yang, Zhijun
    Qiao, Zhi
    Yu, Xianglin
    Yang, Haiyue
    Yuan, Mingquan
    Jin, Yi
    TETRAHEDRON LETTERS, 2024, 147
  • [9] Ruthenium(II)-Catalyzed Oxidative C-H Alkenylations of Sulfonic Acids, Sulfonyl Chlorides and Sulfonamides
    Ma, Wenbo
    Mei, Ruhuai
    Tenti, Giammarco
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (46) : 15248 - 15251
  • [10] Ruthenium-catalyzed, site-selective C-H activation: access to C5-substituted azaflavanone
    Bakthadoss, Manickam
    Reddy, Tadiparthi Thirupathi
    Sharada, Duddu S.
    RSC ADVANCES, 2020, 10 (52) : 31570 - 31574