Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides

被引：47
|
作者：
Couty, S [1 ]
Barbazanges, M [1 ]
Meyer, C [1 ]
Cossy, J [1 ]
机构：
[1] Ecole Super Phys & Chim Ind Ville Paris, Assoc CNRS, Chim Organ Lab, F-75231 Paris, France
来源：
SYNLETT | 2005年 / 06期
关键词：
cross-coupling; palladium; enamides; eliminations; ynamides;
D O I：
10.1055/s-2005-864821
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
beta,beta-Dihaloenamides can be successfully involved in palladium-catalyzed Suzuki-Miyaura coupling reactions. Whereas the resulting trisubstituted (Z)-beta-bromoenamides could participate in a second cross-coupling leading to beta, beta-disubstituted enamides, the (Z)-beta-chloroenamides have been converted to disubstituted ynamides by an E-2 elimination.
引用
收藏
页码：905 / 910
页数：6
相关论文
共 50 条
  • [1] Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides
    Shaoyu Mai
    Wendong Li
    Xue Li
    Yingwei Zhao
    Qiuling Song
    Nature Communications, 10
  • [2] Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides
    Mai, Shaoyu
    Li, Wendong
    Li, Xue
    Zhao, Yingwei
    Song, Qiuling
    NATURE COMMUNICATIONS, 2019, 10 (1)
  • [3] Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters
    Ben Halima, Taoufik
    Zhang, Wanying
    Yalaoui, Imane
    Hong, Xin
    Yang, Yun-Fang
    Houk, Kendall N.
    Newman, Stephen G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) : 1311 - 1318
  • [4] The Origin of Shape Sensitivity in Palladium-Catalyzed Suzuki-Miyaura Cross Coupling Reactions
    Collins, Gillian
    Schmidt, Michael
    Dwyer, Colm O.
    Holmes, Justin D.
    McGlacken, Gerard P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) : 4142 - 4145
  • [5] Arylcalixarenyl Phosphines in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions
    Elaieb, Fethi
    Hedhli, Ahmed
    Semeril, David
    Matt, Dominique
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (10) : 1867 - 1873
  • [6] A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8059 - 8063
  • [7] Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral γ-Butyrolactones
    Stockton, Kieran P.
    Merritt, Christopher J.
    Sumby, Christopher J.
    Greatrex, Ben W.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (32) : 6999 - 7008
  • [8] Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters
    Dardir, Amira H.
    Casademont-Reig, Irene
    Balcells, David
    Ellefsen, Jonathan D.
    Espinosa, Matthew R.
    Hazari, Nilay
    Smith, Nicholas E.
    ORGANOMETALLICS, 2021, 40 (14) : 2332 - 2344
  • [9] Selective Palladium-Catalyzed Suzuki-Miyaura Reactions of Polyhalogenated Heteroarenes
    Rossi, Renzo
    Bellina, Fabio
    Lessia, Marco
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (07) : 1181 - 1255
  • [10] Palladium-Catalyzed Suzuki-Miyaura Coupling Reactions of Boronic Acid Derivatives with Aryl Chlorides
    Zhou, Zihong
    Zhang, Yaqi
    Xia, Wang
    Chen, Huixuan
    Liang, Hao
    He, Xuefeng
    Yu, Sifan
    Cao, Rihui
    Qiu, Liqin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (10) : 1260 - 1268
12345