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
  • [41] Ruthenium-Catalyzed ortho-C-H Mono- and Di-imidation of Arenes with N-Tosyloxyphthalimide
    Yadav, M. Ramu
    Shankar, Majji
    Ramesh, E.
    Ghosh, Koushik
    Sahoo, Akhila K.
    ORGANIC LETTERS, 2015, 17 (08) : 1886 - 1889
  • [42] Mild and efficient palladium-catalyzed fluoroalkylation and fluoroalkenylation of (hetero)aromatic systems by directed ortho-C-H activation
    Toth, Balazs
    Kovacs, Szabolcs
    Egyed, Orsolya
    Benyei, Attila
    Stirling, Andras
    Novak, Zoltan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [43] Microwave-Promoted ortho-C-H Bond (Hetero)arylation of Arylpyrimidines in Water Catalyzed by Ruthenium(II)-Carboxylate
    Drev, Miha
    Groselj, Uros
    Ledinek, Bine
    Perdih, Franc
    Svete, Jurij
    Stefane, Bogdan
    Pozgan, Franc
    CHEMCATCHEM, 2018, 10 (17) : 3824 - 3832
  • [44] A convenient synthesis of anthranilic acids by Pd-catalyzed direct intermolecular ortho-C-H amidation of benzoic acids
    Ng, Ka-Ho
    Ng, Fo-Ning
    Yu, Wing-Yiu
    CHEMICAL COMMUNICATIONS, 2012, 48 (95) : 11680 - 11682
  • [45] Ru(II)-Catalyzed Switchable C-H Alkylation and Spirocyclization of 2-Arylquinoxalines with Maleimides via ortho-C-H Activation
    Laru, Sudip
    Bhattacharjee, Suvam
    Singsardar, Mukta
    Samanta, Sadhanendu
    Hajra, Alakananda
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2784 - 2795
  • [46] Cobalt-Catalyzed ortho-C-H Alkylation of 2-Arylpyridines via Ring-Opening of Aziridines
    Gao, Ke
    Paira, Rupankar
    Yoshikai, Naohiko
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1486 - 1490
  • [47] Transition-Metal-Catalyzed Direct C-H Alkenylation, Alkynylation, Benzylation, and Alkylation of (Hetero)arenes
    Messaoudi, Samir
    Brion, Jean-Daniel
    Alami, Mouad
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (34) : 6495 - 6516
  • [48] Rhodium(III)-Catalyzed ortho-C-H Alkylation of 2-Arylbenzothiazoles and 2-Arylthiazoles with Potassium Alkyltrifluoroborates
    Ping, Yuanyuan
    Chen, Zhaobin
    Ding, Qiuping
    Peng, Yiyuan
    SYNTHESIS-STUTTGART, 2017, 49 (09): : 2015 - 2024
  • [49] Construction of Bulky Ligand Libraries by Ru(II)-Catalyzed P(III)-Assisted ortho-C-H Secondary Alkylation
    Li, Ming
    Tao, Jun-Yang
    Wang, Liang-Neng
    Li, Jia-Wei
    Liu, Yue-Jin
    Zeng, Ming-Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17): : 11915 - 11925
  • [50] Rh(III)-catalyzed highly regioselective construction of spiro-isoindoline frameworks through ortho-C-H activation
    Srinivas, L.
    Chary, D. Yogananda
    Ajay, Ch.
    Sridhar, B.
    Reddy, B. Jagan Mohan
    Reddy, B. V. Subba
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1289
12345