Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts

被引:128
|
作者
Bolshan, Yuri [1 ]
Batey, Robert A. [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
关键词
copper; cross-coupling; enamides; homogeneous catalysis;
D O I
10.1002/anie.200704711
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A new partner: Potassium alkenyltrifluoroborate salts undergo coupling with amides to give enamides in the presence of a Cu(OAc)2 catalyst and under mild oxidative conditions (see scheme). The air- and water-stable alkenyltrifluoroborate salts offer a convenient alternative to alkenyl halides as cross-coupling partners. A range of amides undergo coupling including cyclic amides, imides, and carbamates as well as benzamides. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2109 / 2112
页数:4
相关论文
共 50 条
  • [41] Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400
    Chen, Junmin
    Zhang, Yimin
    Hao, Wenyan
    Zhang, Rongli
    Yi, Fei
    TETRAHEDRON, 2013, 69 (02) : 613 - 617
  • [42] Copper-catalyzed C-P cross-coupling of arylmethyl quaternary ammonium salts via C-N bond cleavage
    Li, Nutao
    Chen, Feng
    Wang, Guanghui
    Zeng, Qingle
    MONATSHEFTE FUR CHEMIE, 2020, 151 (01): : 99 - 106
  • [43] A convenient and direct route to phosphinoalkynes via copper-catalyzed cross-coupling of terminal alkynes with chlorophosphanes
    Afanasiev, VV
    Beletskaya, IP
    Kazankova, MA
    Efimova, IV
    Antipin, MU
    SYNTHESIS-STUTTGART, 2003, (18): : 2835 - 2838
  • [44] Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water
    Chen, Yi-An
    Badsara, Satpal Singh
    Tsai, Wan-Ting
    Lee, Chin-Fa
    SYNTHESIS-STUTTGART, 2015, 47 (02): : 181 - 186
  • [45] Copper-Catalyzed Synthesis of Weinreb Amides by Oxidative Amidation of Alcohols
    Yedage, Subhash L.
    Bhanage, Bhalchandra M.
    SYNTHESIS-STUTTGART, 2015, 47 (04): : 526 - 532
  • [46] Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides
    Liu, Jing-Hui
    Yang, Chu-Ting
    Lu, Xiao-Yu
    Zhang, Zhen-Qi
    Xu, Ling
    Cui, Mian
    Lu, Xi
    Xiao, Bin
    Fu, Yao
    Liu, Lei
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (47) : 15334 - 15338
  • [47] Palladium-free copper-catalyzed Sonogashira cross-coupling at room temperature
    Liang, Huimin
    Fu, Hua
    Qiao, Renzhong
    Jiang, Yuyang
    Zhao, Yufen
    SYNTHESIS-STUTTGART, 2008, (15): : 2417 - 2426
  • [48] Copper-catalyzed cross-coupling of aryl halides and thiols using microwave heating
    Wu, YJ
    He, H
    SYNLETT, 2003, (12) : 1789 - 1790
  • [49] Recent advances in copper-catalyzed C-S cross-coupling reactions
    Sujatha, Asha
    Thomas, Anns Maria
    Thankachan, Amrutha P.
    Anilkumar, Gopinathan
    ARKIVOC, 2015, : 1 - 28
  • [50] Transmetalation of Alkylzirconocenes in Copper-Catalyzed Alkyl-Alkynyl Cross-Coupling Reactions
    Indukuri, Kiran
    Riant, Olivier
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) : 2425 - 2433