Rh(III)-Catalyzed Decarboxylative ortho-Heteroarylation of Aromatic Carboxylic Acids by Using the Carboxylic Acid as a Traceless Directing Group

被引:103
|
作者
Qin, Xurong [1 ,2 ,3 ]
Sun, Denan [1 ,2 ]
You, Qiulin [1 ,2 ]
Cheng, Yangyang [1 ,2 ]
Lan, Jingbo [1 ,2 ]
You, Jingsong [1 ,2 ]
机构
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
[2] Sichuan Univ, West China Med Sch, State Key Lab Biotherapy, Chengdu 610064, Peoples R China
[3] Southwest Univ, Coll Pharmaceut Sci, Chongqing 400716, Peoples R China
关键词
C-H FUNCTIONALIZATION; DIRECT ARYLATION; BENZOIC-ACIDS; CONVENIENT SYNTHESIS; SIMPLE ARENES; RHODIUM; ARYL; DERIVATIVES; THIOPHENES; AMIDATION;
D O I
10.1021/acs.orglett.5b00532
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly selective decarboxylative ortho-heteroarylation of aromatic carboxylic acids with various heteroarenes has been developed through Rh(III)-catalyzed two-fold C-H activation, which exhibits a wide substrate scope of both aromatic carboxylic acids and heteroarenes. The use of naturally occurring carboxylic acid as the directing group avoids troublesome extra steps for installation and removal of an external directing group.
引用
收藏
页码:1762 / 1765
页数:4
相关论文
共 50 条
  • [41] Rhodium(III)-Catalyzed Intramolecular Olefin Hydroarylation of Aromatic Aldehydes Using a Transient Directing Group
    Guan, Zhe
    Chen, Siwei
    Huang, Yue
    Yao, Hequan
    ORGANIC LETTERS, 2019, 21 (11) : 3959 - 3962
  • [42] Iridium-Catalyzed, Weakly Coordination-Assisted Ortho-Alkynylation of (Hetero)aromatic Carboxylic Acids without Cyclization
    Chen, Changpeng
    Liu, Pei
    Tang, Jinghua
    Deng, Gongda
    Zeng, Xiaoming
    ORGANIC LETTERS, 2017, 19 (10) : 2474 - 2477
  • [43] Palladium-Catalyzed C-H Functionalization of Ferrocene-carboxylic Acid by using 8-Aminoquinoline as a Removable Directing Group
    Sattar, Moh.
    Praveen
    Prasad, Ch. Durga
    Verma, Ajay
    Kumar, Shailesh
    Kumar, Sangit
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 240 - 253
  • [44] PALLADIUM CATALYZED ELECTROSYNTHESIS USING ARYL TRIFLUOROMETHANESULFONATES (TRIFLATES) - SYNTHESIS OF BIARYLS AND AROMATIC CARBOXYLIC-ACIDS
    JUTAND, A
    NEGRI, S
    MOSLEH, A
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (23) : 1729 - 1730
  • [45] Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
    Dai, Ling
    Yu, Shuling
    Lv, Ningning
    Ye, Xuanzeng
    Shao, Yinlin
    Chen, Zhongyan
    Chen, Jiuxi
    ORGANIC LETTERS, 2021, 23 (15) : 5664 - 5668
  • [46] Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C-H Activation: A Facile Access to Diverse Indolo[1,2-a]quinolines
    Liu, Xingyan
    Li, Xiaoyu
    Liu, Hu
    Guo, Qiang
    Lan, Jingbo
    Wang, Ruilin
    You, Jingsong
    ORGANIC LETTERS, 2015, 17 (12) : 2936 - 2939
  • [47] Cobalt-Catalyzed C(sp2)-H Carbonylation of Amino Acids Using Picolinamide as a Traceless Directing Group
    Lukasevics, Lukass
    Cizikovs, Aleksandrs
    Grigorjeva, Liene
    ORGANIC LETTERS, 2021, 23 (07) : 2748 - 2753
  • [48] Cobalt(III)-Catalyzed C-H Activation: A Secondary Amide Directed Decarboxylative Functionalization of Alkynyl Carboxylic Acids Wherein Amide NH-group Remains Unreactive
    Muniraj, Nachimuthu
    Prabhu, Kandikere Ramaiah
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) : 1370 - 1375
  • [49] Rhodium(III)-catalyzed ortho-alkenylation using a cyclic N-phosphoryl ketimine as the directing group
    Zhu, Yu-Qin
    Qin, Liu
    Song, Qiang
    Su, Fu
    Xu, Yan-Jun
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (40) : 9472 - 9475
  • [50] Directing Group in Decarboxylative Cross-Coupling: CopperCatalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids
    Liu, Zhao-Jing
    Lu, Xi
    Wang, Guan
    Li, Lei
    Jiang, Wei-Tao
    Wang, Yu-Dong
    Xiao, Bin
    Fu, Yao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (30) : 9714 - 9719