Palladium-Catalyzed Decarboxylative Coupling of Quinolinone-3-Carboxylic Acids and Related Heterocyclic Carboxylic Acids with (Hetero)aryl Halides

被引：74
|
作者：
Messaoudi, Samir [1 ]
Brion, Jean-Daniel [1 ]
Alami, Mouad [1 ]
机构：
[1] Univ Paris 11, Fac Pharm, Chim Therapeut Lab, LabEX LERMIT,CNRS,BioCIS UMR 8076, F-92296 Chatenay Malabry, France
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 06期
关键词：
BIARYL SYNTHESIS; ARYL HALIDES; INHIBITORS; NOVOBIOCIN; BROMIDES; AGENTS;
D O I：
10.1021/ol300235k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and practical decarboxylative cross-coupling reaction of quinolin-4(1H)-one 3-carboxylic acids with (hetero)aryl halides has been established. Under a bimetallic system of PdBr2 and silver carbonate, the protocol proved to be general, and a variety of 3-(hetero)aryl 4-quinolinones and related heterocycles, such as 3-aryl-1,8-naphthyridin-4(1H)-ones, 3-arylcoumarins, 3-arylquinolin-2(1H)-ones, and 2-arylchromones, can be prepared in good to excellent yields.
引用
收藏
页码：1496 / 1499
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides
    Moon, Jeongju
    Jang, Mihee
    Lee, Sunwoo
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03): : 1403 - 1406
  • [2] Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Benzyl Halides or Aryl Halides
    Zhang, Wen-Wu
    Zhang, Xing-Guo
    Li, Jin-Heng
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5259 - 5264
  • [3] Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates
    Lee, Ju-Hyeon
    Raja, Gabriel Charles Edwin
    Yu, Subeen
    Lee, Junseong
    Song, Kwang Ho
    Lee, Sunwoo
    ACS OMEGA, 2017, 2 (09): : 6259 - 6269
  • [4] Palladium-catalyzed decarboxylative coupling of ,-unsaturated carboxylic acids with aryl tosylates
    Zhang, Wei
    Chen, Gairong
    Wang, Kaikai
    Xia, Ran
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (06)
  • [5] Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides
    Bilodeau, Francois
    Brochu, Marie-Christine
    Guimond, Nicolas
    Thesen, Kris H.
    Forgione, Pat
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05): : 1550 - 1560
  • [6] Palladium-Catalyzed Decarboxylative Trifluoroethylation of Aryl Alkynyl Carboxylic Acids
    Hwang, Jinil
    Park, Kyungho
    Choe, Juseok
    Min, Hongkeun
    Song, Kwang Ho
    Lee, Sunwoo
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07): : 3267 - 3271
  • [7] Palladium-Catalyzed Intramolecular Decarboxylative Coupling of Arene Carboxylic Acids/Esters with Aryl Bromides
    Shen, Zengming
    Ni, Zhenjie
    Mo, Song
    Wang, Jing
    Zhu, Yamin
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) : 4859 - 4865
  • [8] Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes
    Jang, Jisun
    Charles, Gabriel
    Raja, Edwin
    Lee, Ju-Hyeon
    Son, Yujeong
    Kim, Jimin
    Lee, Sunwoo
    TETRAHEDRON LETTERS, 2016, 57 (41) : 4581 - 4584
  • [9] Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids
    Feng, Chao
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4779 - 4781
  • [10] Ligand-free palladium-catalyzed decarboxylative coupling reactions of aryl iodides and alkynyl carboxylic acids
    Pyo, Ayoung
    Kim, Ji Dang
    Choi, Hyun Chul
    Lee, Sunwoo
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 724 : 271 - 274
12345