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
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 07期
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
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  • [1] Chlorizidine, a Cytotoxic 5H-Pyrrolo[2,1-a]isoindol-5-one-Containing Alkaloid from a Marine Streptomyces sp.
    Alvarez-Mico, Xavier
    Jensen, Paul R.
    Fenical, William
    Hughes, Chambers C.
    [J]. ORGANIC LETTERS, 2013, 15 (05) : 988 - 991
  • [2] Synthesis of Aryl Ethers from Benzoates through Carboxylate-Directed C-H-Activating Alkoxylation with Concomitant Protodecarboxylation
    Bhadra, Sukalyan
    Dzik, Wojciech I.
    Goossen, Lukas J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (10) : 2959 - 2962
  • [3] Two methods for direct ortho-arylation of benzoic acids
    Chiong, Hendrich A.
    Pham, Quynh-Nhu
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) : 9879 - 9884
  • [4] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes
    Cho, Seung Hwan
    Hwang, Seung Jun
    Chang, Sukbok
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9254 - +
  • [5] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
    Cho, Seung Hwan
    Kim, Ji Young
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
  • [6] Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation
    Cornella, Josep
    Righi, Marika
    Larrosa, Igor
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) : 9429 - 9432
  • [7] Intermolecular Decarboxylative Direct C-3 Arylation of Indoles with Benzoic Acids
    Cornella, Josep
    Lu, Pengfei
    Larrosa, Igor
    [J]. ORGANIC LETTERS, 2009, 11 (23) : 5506 - 5509
  • [8] Development of a catalytic aromatic decarboxylation reaction
    Dickstein, Joshua S.
    Mulrooney, Carol A.
    O'Brien, Erin M.
    Morgan, Barbara J.
    Kozlowski, Marisa C.
    [J]. ORGANIC LETTERS, 2007, 9 (13) : 2441 - 2444
  • [9] An Aromatic Glaser-Hay Reaction
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (47) : 17052 - +
  • [10] Rhodium or Ruthenium-Catalyzed Oxidative C?H/C?H Cross-Coupling: Direct Access to Extended p-Conjugated Systems
    Dong, Jiaxing
    Long, Zhen
    Song, Feijie
    Wu, Ningjie
    Guo, Qiang
    Lan, Jingbo
    You, Jingsong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) : 580 - 584
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