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
  • [31] Tetrabutylammonium Bifluoride as an Efficient Activating Agent for Copper-Catalyzed Vinylsilane Cross-Coupling Reactions
    Cornelissen, Loic
    Nagy, Audric
    Leyssens, Tom
    Riant, Olivier
    SYNLETT, 2017, 28 (18) : 2465 - 2467
  • [32] Synthesis of Pyrrole-Annulated Heterocycles through Copper-Catalyzed Site-Selective Dehydrogenative Cross-Coupling
    Tripathi, Krishna N.
    Ray, Devalina
    Singh, Ravi P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (38) : 5809 - 5813
  • [33] Copper-catalyzed Cross-coupling Reaction between Aryl(trialkyl)silanes and Alkyl Halides
    Komiyama, Takeshi
    Minami, Yasunori
    Hiyama, Tamejiro
    CHEMISTRY LETTERS, 2018, 47 (08) : 1048 - 1050
  • [34] A General and Selective Copper-Catalyzed Cross-Coupling of Tertiary Grignard Reagents with Azacyclic Electrophiles
    Hintermann, Lukas
    Xiao, Li
    Labonne, Aurelie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) : 8246 - 8250
  • [35] Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides
    Yang, Chu-Ting
    Zhang, Zhen-Qi
    Liu, Yu-Chen
    Liu, Lei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3904 - 3907
  • [36] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles
    Altenhoff, G
    Glorius, F
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1661 - 1664
  • [37] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary Amides into oxazoles
    Schuh, Kerstin
    Glorius, Frank
    SYNTHESIS-STUTTGART, 2007, (15): : 2297 - 2306
  • [38] Copper-catalyzed oxidative coupling of carboxylic acids with formamides for the synthesis of α,β-unsaturated amides
    Li, Huamin
    Pan, Changduo
    Cheng, Yixiang
    Zhu, Chengjian
    TETRAHEDRON LETTERS, 2013, 54 (49) : 6679 - 6681
  • [39] Pd/C-Catalyzed Cross-Coupling of Arenediazonium Salts with Potassium Aryltrifluoroborates
    Varnedoe, Lee S.
    Angel, Brad D.
    McClellan, Joshua L.
    Hanna, James M., Jr.
    LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (01) : 1 - 6
  • [40] Copper-Catalyzed Asymmetric Oxidative Cross-Coupling of 2-Naphthols with Aryl Methyl Ketones
    Deng, Tao
    Wang, Hongjun
    Cai, Chun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) : 1569 - 1574