A facile method for Rh-catalyzed decarbonylative ortho-C-H alkylation of (hetero)arenes with alkyl carboxylic acids

被引：1
|
作者：
Tian, Yiqiang [1 ,2 ]
Liu, Xiaojie [1 ,2 ]
He, Bangyue [2 ]
Ren, Yuxi [2 ]
Su, Weiping [2 ]
机构：
[1] Fuzhou Univ, Coll Chem, Fuzhou 350116, Peoples R China
[2] Chinese Acad Sci, State Key Lab Struct Chem, Ctr Excellence Mol Synth, Fujian Inst Res Struct Matter, Fuzhou 350002, Peoples R China
来源：
RSC ADVANCES | 2021年 / 11卷 / 32期
基金：
中国国家自然科学基金;
关键词：
TRANSIENT DIRECTING GROUPS; BOND FORMATION; POSSIBLE GENERATION; AROMATIC AMIDES; FUNCTIONALIZATION; DECARBOXYLATION; CARBOXAMIDES; ACTIVATION; PHOTOREDOX; HALIDES;
D O I：
10.1039/d1ra03992j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile and effective method for Rh-catalyzed direct ortho-alkylation of C-H bonds in (hetero)arenes with commercially available carboxylic acids has been developed. This strategy was initiated by in situ conversion of carboxylic acids to anhydrides which, without isolation, underwent Rh-catalyzed direct decarbonylative cross-coupling of aryl carboxamides containing 8-aminoquinoline. The reaction proceeds with high regioselectivity and exhibits a broad substrate scope as well as functional group tolerance.
引用
收藏
页码：19827 / 19831
页数：5
相关论文
共 50 条
  • [31] Ligand-enabled ruthenium-catalyzed meta-C-H alkylation of (hetero)aromatic carboxylic acids
    Luo, Xianglin
    Hou, Peichao
    Shen, Jiayi
    Kuang, Yifeng
    Sun, Fengchao
    Jiang, Huanfeng
    Goossen, Lukas J.
    Huang, Liangbin
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [32] Pd-Catalyzed Monoselective ortho-C-H Alkylation of N-Quinolyl Benzamides: Evidence for Stereoretentive Coupling of Secondary Alkyl Iodides
    Zhang, Shu-Yu
    Li, Qiong
    He, Gang
    Nack, William A.
    Chen, Gong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 531 - 539
  • [33] Ruthenaphoto-catalyzed ortho-C-H alkylation with secondary alkyl halides: SET-enabled ruthenium(II/III/IV) manifold
    Wang, Yulei
    Yuan, Binbin
    Chang, Xuexue
    Ackermann, Lutz
    CHEM, 2025, 11 (01):
  • [34] Rhodium-catalysed decarbonylative C(sp2)-H alkylation of indolines with alkyl carboxylic acids and carboxylic anhydrides under redox-neutral conditions
    Suzuki, Hirotsugu
    Kawai, Yuya
    Takemura, Yosuke
    Matsuda, Takanori
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (14) : 2808 - 2812
  • [35] Palladium-Catalyzed Oxidative Direct ortho-C-H Acylation of Arenes with Aldehydes under Aqueous Conditions
    Xiao, Fuhong
    Chen, Shuqing
    Huang, Huawen
    Deng, Guo-Jun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (36) : 7919 - 7925
  • [36] Rh-Catalyzed General Method for Directed C-H Functionalization via Decarbonylation of in-Situ-Generated Acid Fluorides from Carboxylic Acids
    He, Bangyue
    Liu, Xiaojie
    Li, Hongyi
    Zhang, Xiaofeng
    Ren, Yuxi
    Su, Weiping
    ORGANIC LETTERS, 2021, 23 (11) : 4191 - 4196
  • [37] Rh-Catalyzed Ortho-Selective C-H Borylatiob of N-Functionalized Arenes with Silica-Supported Bridgehead Monophosphine Ligands
    Kawamorita, Soichiro
    Miyazaki, Tatsuya
    Ohmiya, Hirohisa
    Iwai, Tomohiro
    Sawamura, Masaya
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) : 19310 - 19313
  • [38] Palladium( II)-Catalyzed ortho-C-H Arylation/Alkylation of N-Benzoyl α-Amino Ester Derivatives
    Castro, Luis C. Misal
    Chatani, Naoto
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (16) : 4548 - 4553
  • [39] Co-catalyzed ortho-C-H functionalization/annulation of arenes and alkenes with alkynylsilanes: access to isoquinolone and pyridone motifs
    Lin, Cong
    Shen, Liang
    RSC ADVANCES, 2019, 9 (53) : 30650 - 30654
  • [40] Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines
    Nack, William A.
    Wang, Xinmou
    Wang, Bo
    He, Gang
    Chen, Gong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1243 - 1249
12345