Rh-Catalyzed General Method for Directed C-H Functionalization via Decarbonylation of in-Situ-Generated Acid Fluorides from Carboxylic Acids

被引：10
作者：
He, Bangyue [1 ,2 ]
Liu, Xiaojie [1 ]
Li, Hongyi [1 ]
Zhang, Xiaofeng [1 ]
Ren, Yuxi [1 ]
Su, Weiping [1 ,2 ]
机构：
[1] Chinese Acad Sci, Ctr Excellence Mol Synth, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 11期
基金：
中国国家自然科学基金;
关键词：
DECARBOXYLATION; ALKYLATION; ACTIVATION; ARYLATION; AMIDES; BONDS;
D O I：
10.1021/acs.orglett.1c01103
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Rh-catalyzed decarbonylative C-H coupling of in-situ-generated acid fluorides with amide substrates bearing ortho-Csp(2)-H bonds has been developed. This method enables alkyl, aryl, and alkenyl carboxylic acids to undergo decarbonylative coupling with C-H bonds of (hetero)aromatic or alkenyl amides in generally good yields via the in situ conversion of carboxylic acids into acid fluorides and also allows for the functionalization of a series of structurally complex carboxyl-containing natural products and pharmaceuticals as well as pharmaceutical amide derivatives.
引用
收藏
页码：4191 / 4196
页数：6
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  • [1] Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance
    Aihara, Yoshinori
    Chatani, Naoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5308 - 5311
  • [2] Acid Fluorides in Transition-Metal Catalysis: A Good Balance between Stability and Reactivity
    Blanchard, Nicolas
    Bizet, Vincent
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (21) : 6814 - 6817
  • [3] Why Are (NN2)Ni Pincer Complexes Active for Alkyl-Alkyl Coupling: β-H Elimination Is Kinetically Accessible but Thermodynamically Uphill
    Breitenfeld, Jan
    Vechorkin, Oleg
    Corminboeuf, Clemence
    Scopelliti, Rosario
    Hu, Xile
    [J]. ORGANOMETALLICS, 2010, 29 (17) : 3686 - 3689
  • [4] Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
    Candish, L.
    Freitag, M.
    Gensch, T.
    Glorius, F.
    [J]. CHEMICAL SCIENCE, 2017, 8 (05) : 3618 - 3622
  • [5] Ligand-Controlled Chemoselective C(acyl)-O Bond vs Caryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings
    Chatupheeraphat, Adisak
    Liao, Hsuan-Hung
    Srimontree, Watchara
    Guo, Lin
    Minenkov, Yury
    Poater, Albert
    Cavallo, Luigi
    Rueping, Magnus
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (10) : 3724 - 3735
  • [6] Transition-Metal-Catalyzed C-H Alkylation Using Alkenes
    Dong, Zhe
    Ren, Zhi
    Thompson, Samuel J.
    Xu, Yan
    Dong, Guangbin
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9333 - 9403
  • [7] Beyond Friedel and Crafts: Directed Alkylation of C-H Bonds in Arenes
    Evano, Gwilherm
    Theunissen, Cedric
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) : 7202 - 7236
  • [8] Synthesis of biaryls via catalytic decarboxylative coupling
    Goossen, Lukas J.
    Deng, Guojun
    Levy, Laura M.
    [J]. SCIENCE, 2006, 313 (5787) : 662 - 664
  • [9] Transition-Metal-Catalyzed Decarbonylative Coupling Reactions: Concepts, Classifications, and Applications
    Guo, Lin
    Rueping, Magnus
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (31) : 7794 - 7809
  • [10] A General Pd-Catalyzed Decarboxylative Cross-Coupling Reaction between Aryl Carboxylic Acids: Synthesis of Biaryl Compounds
    Hu, Peng
    Shang, Yaping
    Su, Weiping
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) : 5945 - 5949
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