Palladium-catalyzed synthesis of biaryls from arylzinc compounds using N-chlorosuccinimide or oxygen as an oxidant

被引:20
作者
Hossain, KM [1 ]
Kameyama, T [1 ]
Shibata, T [1 ]
Takagi, K [1 ]
机构
[1] Okayama Univ, Fac Sci, Dept Chem, Okayama 7008530, Japan
关键词
D O I
10.1246/bcsj.74.2415
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of a catalytic amount of Pd2+ or Pd-0, oxidative homo-coupling of arylzinc compounds was achieved by the use of N-chlorosuccinimide (NCS) or O-2 as an oxidant. Different reaction pathways were involved in the catalytic reactions depending on the oxidants; NCS or O-2 probably oxidized I- or Pd-0 to I+ or Pd2+, respectively. This reaction disclosed a new and facile synthetic method of biaryls from aryl halides or arenes via arylzinc intermediates.
引用
收藏
页码:2415 / 2420
页数:6
相关论文
共 65 条
  • [1] Alcaraz L, 1997, SYNLETT, P791
  • [2] Electrospray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids
    Aramendía, MA
    Lafont, F
    Moreno-Mañas, M
    Pleixats, R
    Roglans, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) : 3592 - 3594
  • [3] BADUBRI F, 1997, J ORG CHEM, V62, P3291
  • [4] Oligothiophene S,S-dioxides.: Synthesis and electronic properties in relation to the parent oligothiophenes
    Barbarella, G
    Favaretto, L
    Sotgiu, G
    Zambianchi, M
    Antolini, L
    Pudova, O
    Bongini, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) : 5497 - 5506
  • [5] A NEW AND EFFICIENT REACTION FOR THE SYNTHESIS OF THE CARBON-CARBON BOND
    BARTON, DHR
    OZBALIK, N
    RAMESH, M
    [J]. TETRAHEDRON LETTERS, 1988, 29 (29) : 3533 - 3536
  • [6] THE CHEMISTRY OF ORGANOBISMUTH REAGENTS .13. LIGAND COUPLING INDUCED BY PD(0)
    BARTON, DHR
    OZBALIK, N
    RAMESH, M
    [J]. TETRAHEDRON, 1988, 44 (18) : 5661 - 5668
  • [7] A GENERAL-METHOD FOR THE COUPLING OF VINYL STANNANES
    BEDDOES, RL
    CHEESERIGHT, T
    WANG, JY
    QUAYLE, P
    [J]. TETRAHEDRON LETTERS, 1995, 36 (02) : 283 - 286
  • [8] BLOCK E, 1991, COMPREHENSIVE ORGANI, V4, P355
  • [9] EASY OXIDATION OF ORGANOZINC COMPOUNDS TO ALCOHOLS
    CHEMLA, F
    NORMANT, J
    [J]. TETRAHEDRON LETTERS, 1995, 36 (18) : 3157 - 3160
  • [10] COLLMAN JP, 1987, PRINCIPLES APPL ORGA, P710