Palladacycle-Catalyzed Deacetonative Sonogashira Coupling of Aryl Propargyl Alcohols with Aryl Chlorides

被引：52
|
作者：
Hu, Hao [1 ]
Yang, Fan [1 ]
Wu, Yangjie [1 ]
机构：
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Zhengzhou 450052, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期
基金：
中国国家自然科学基金;
关键词：
ALKYNYL CARBOXYLIC-ACIDS; ONE-POT SYNTHESIS; TERMINAL ALKYNES; PALLADIUM; EFFICIENT; DIARYLALKYNES; HALIDES; CARBON;
D O I：
10.1021/jo4014657
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and general protocol for the deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides is described. The reaction proceeded smoothly with the catalyst system of palladacycle/Xphos. This result represents the first successful deacetonative Sonogashira version for electron-poor, electron-neutral, and even inactive sterically hindered electron-rich aryl chlorides.
引用
收藏
页码：10506 / 10511
页数：6
相关论文
共 50 条
  • [11] A Practical Heterogeneous Catalyst for the Suzuki, Sonogashira, and Stille Coupling Reactions of Unreactive Aryl Chlorides
    Jin, Myung-Jong
    Lee, Dong-Hwan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (06) : 1119 - 1122
  • [12] Copper-Free Oxime-Palladacycle-Catalyzed Sonogashira Alkynylation of Deactivated Aryl Bromides and Chlorides in Water under Microwave Irradiation
    Buxaderas, Eduardo
    Alonso, Diego A.
    Najera, Carmen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (26) : 5864 - 5870
  • [13] Aryl Chlorides as Coupling Partners in the Palladium-catalyzed Decarboxylative Coupling Reactions of Propiolic Acids
    Lee, Ju-Hyeon
    Raja, Gabriel Charles Edwin
    Kim, Jimin
    Nam, Kye Chun
    Lee, Sunwoo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2017, 38 (11): : 1368 - 1371
  • [14] Highly Active Palladium Catalyst for the Sonogashira Coupling Reaction of Unreactive Aryl Chlorides
    Lee, Dong-Hwan
    Kwon, Young-Jun
    Jin, Myung-Jong
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (17) : 3090 - 3094
  • [15] A General Palladium-Catalyzed Sonogashira Coupling of Aryl and Heteroaryl Tosylates
    R'kyek, Omar
    Halland, Nis
    Lindenschmidt, Andreas
    Alonso, Jorge
    Lindemann, Peter
    Urmann, Matthias
    Nazare, Marc
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 9986 - 9989
  • [16] Palladium-catalyzed cyclocotrimerization of propargyl alcohols with aryl halides
    Oi, S
    Orihara, H
    Kawai, H
    Inoue, Y
    HETEROCYCLES, 2005, 66 : 621 - 625
  • [17] Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols
    Yu, Hang
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (44) : 9723 - 9731
  • [18] A General Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Triflates
    Wu, Xiao-Feng
    Sundararaju, Basker
    Neumann, Helfried
    Dixneuf, Pierre H.
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) : 106 - 110
  • [19] Manganese-catalyzed oxidative homo-coupling of aryl Grignard chlorides
    Zhou, Zhiming
    Xue, Weizhe
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (05) : 599 - 603
  • [20] Synthesis of diarylalkynes via tandem Sonogashira/decarboxylative reaction of aryl chlorides with propiolic acid
    Li, Xiang
    Yang, Fan
    Wu, Yangjie
    RSC ADVANCES, 2014, 4 (26): : 13738 - 13741
12345