Oxygen-promoted Pd(II) catalysis for the coupling of organoboron compounds and olefins

被引:145
作者
Jung, YC [1 ]
Mishra, RK [1 ]
Yoon, CH [1 ]
Jung, KW [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
关键词
D O I
10.1021/ol034458s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported herein is a mild and efficient Pd(II) catalysis, leading to the formation of carbon-carbon bonds between a broad spectrum of organoboron compounds and alkenes. Molecular oxygen was employed to reoxidize the resultant Pd(0) species back to Pd(II) during catalytic cycles. This oxygen protocol promoted the desired Pd(II) catalysis, whereas it retarded competing Pd(0) catalytic pathways such as Heck or Suzuki couplings.
引用
收藏
页码:2231 / 2234
页数:4
相关论文
共 46 条
  • [1] BARNES JM, 1968, ORGANOMET CHEM REV A, V3, P137
  • [2] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [3] Beritic T, 1970, Arh Hig Rada Toksikol, V21, P285
  • [4] Bianchi D, 1999, ANGEW CHEM INT EDIT, V38, P706, DOI 10.1002/(SICI)1521-3773(19990301)38:5<706::AID-ANIE706>3.0.CO
  • [5] 2-G
  • [6] CHAU YK, 1981, NBS SPEC PUBL, V618, P65
  • [7] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL AND ALKENYL BORONIC ACIDS WITH ALKENES VIA OXIDATIVE ADDITION OF A CARBON-BORON BOND TO PALLADIUM(0)
    CHO, CS
    UEMURA, S
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 465 (1-2) : 85 - 92
  • [8] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB
    DE MEIJERE, A
    MEYER, FE
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) : 2379 - 2411
  • [9] Mizoroki-heck type reaction of organoboron reagents with alkenes and alkynes.: A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant
    Du, XL
    Suguro, M
    Hirabayashi, K
    Mori, A
    Nishikata, T
    Hagiwara, N
    Kawata, K
    Okeda, T
    Wang, HF
    Fugami, K
    Kosugi, M
    [J]. ORGANIC LETTERS, 2001, 3 (21) : 3313 - 3316
  • [10] Fugami K, 1998, SYNLETT, P477