Palladium-Catalysed Carbonylative Cross-Coupling Reactions of Aryl Iodides and Vinyl Boron Derivatives as a Straightforward Route to Aryl Vinyl Ketones

被引:11
|
作者
Pirez, Cyril [1 ]
Dheur, Julien [1 ]
Sauthier, Mathieu [1 ]
Castanet, Yves [1 ]
Mortreux, Andre [1 ]
机构
[1] Univ Sci & Technol Lille 1, Unite Catalyse & Chim Solide, UMR CNRS 8181, ENSCL, F-59652 Villeneuve Dascq, France
关键词
carbonylation; cross-coupling; palladium; vinyl boron derivatives; enones; ARYLBORONIC ACIDS; PYRIDINE HALIDES; POTASSIUM VINYLTRIFLUOROBORATE; CARBENE;
D O I
10.1055/s-0029-1217379
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The carbonylative cross-coupling of potassium vinyl trifluoroborate or 2,4,6-trivinyltricycloboroxane with aryl iodides under mild conditions affords aryl vinyl ketones. The optimisation of the reaction conditions leads to the targeted enones in good yields in the case of the aryl substrates bearing donor substituents in meta or para position. Much more moderate yields were observed with aryl substrates bearing withdrawing substituents.
引用
收藏
页码:1745 / 1748
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalysed Direct Cross-Coupling of Organolithium Reagents with Aryl and Vinyl Triflates
    Vila, Carlos
    Hornillos, Valentin
    Giannerini, Massimo
    Fananas-Mastral, Martin
    Feringa, Ben L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (41) : 13078 - 13083
  • [2] Palladium-catalyzed cross-coupling reactions of triorganoindium compounds with vinyl and aryl triflates or iodides
    Pérez, I
    Sestelo, JP
    Sarandeses, LA
    ORGANIC LETTERS, 1999, 1 (08) : 1267 - 1269
  • [3] Palladium-catalyzed cross-coupling of aryl or vinyl iodides with ethyl diazoacetate
    Peng, Cheng
    Cheng, Jiajia
    Wang, Jianbo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) : 8708 - +
  • [4] Palladium-catalyzed cross-coupling of aryl or vinyl iodides with ethyl diazoacetate
    Peng, Cheng
    Cheng, Jiajia
    Wang, Jianbo
    Journal of the American Chemical Society, 2007, 129 (28): : 8708 - 8709
  • [5] PALLADIUM(0)-PROMOTED CROSS-COUPLING OF ALLENYLMETAL COMPOUNDS WITH ARYL AND VINYL IODIDES - A NOVEL ROUTE TO ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ALLENES
    RUITENBERG, K
    KLEIJN, H
    MEIJER, J
    OOSTVEEN, EA
    VERMEER, P
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 224 (04) : 399 - 405
  • [6] Palladium-catalysed intramolecular coupling of vinyl or aryl halides and β,γ-unsaturated nitronates
    Solé, D
    Urbaneja, X
    Bonjoch, J
    TETRAHEDRON LETTERS, 2004, 45 (15) : 3131 - 3135
  • [7] Palladium-catalyzed carbonylative coupling of aryl iodides with an organocopper reagent: a straightforward procedure for the synthesis of aryl trifluoromethyl ketones
    Zhu, Fengxiang
    Yang, Guangfu
    Zhou, Shaolin
    Wu, Xiao-Feng
    RSC ADVANCES, 2016, 6 (62) : S7070 - S7074
  • [8] CARBONYLATIVE CROSS-COUPLING REACTION OF ARYL IODIDES WITH ALKYLALUMINUMS BY PALLADIUM COMPLEX CATALYSIS
    WAKITA, Y
    YASUNAGA, T
    KOJIMA, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 288 (03) : 261 - 268
  • [9] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF VINYL AND ARYL TRIFLATES WITH TETRAARYLBORATES
    CIATTINI, PG
    MORERA, E
    ORTAR, G
    TETRAHEDRON LETTERS, 1992, 33 (33) : 4815 - 4818
  • [10] Carbonylative cross-coupling reaction of ethynylstibane with aryl iodides
    Kakusawa, Naokl
    Kurita, Jyojt
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (05) : 699 - 702