Palladium-catalyzed addition of alcohol pronucleophiles to alkylidenecyclopropanes

被引:100
作者
Camacho, DH
Nakamura, I
Saito, S
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Inst Chem React Sci, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/jo001428j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed addition of alcohol pronucleophiles 1 to alkylidenecyclopropane derivatives 2 afforded the corresponding allylic ethers 3 in excellent to moderate yields. Catalyst optimization indicated the Pd(PPh3)(4)-P(o-tolyl)(3) combination as the best system among all catalysts tested. Intramolecular reaction also proceeded smoothly. A plausible mechanism for this catalytic reaction was proposed.
引用
收藏
页码:270 / 275
页数:6
相关论文
共 57 条
  • [1] Palladium-catalyzed hydrocarboxylation of allenes
    Al-Masum, M
    Yamamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) : 3809 - 3810
  • [2] The two component palladium catalyst system for intermolecular hydroamination of allenes
    AlMasum, M
    Meguro, M
    Yamamoto, Y
    [J]. TETRAHEDRON LETTERS, 1997, 38 (34) : 6071 - 6074
  • [3] NICKEL-CATALYZED AND PALLADIUM-CATALYZED ADDITIONS OF NUCLEOPHILES TO CYCLIC 1,3-DIENES
    ANDELL, OS
    BACKVALL, JE
    MOBERG, C
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (03): : 184 - 189
  • [4] PALLADIUM-CATALYZED ADDITIONS OF AMINES TO CONJUGATED DIENES - ALTERATION OF BEHAVIOR OF (TRIPHENYLPHOSPHINE)PALLADIUM CATALYSTS WITH AMINE HYDROIODIDE SALTS
    ARMBRUSTER, RW
    MORGAN, MM
    SCHMIDT, JL
    LAU, CM
    RILEY, RM
    ZABROWSKI, DL
    DIECK, HA
    [J]. ORGANOMETALLICS, 1986, 5 (02) : 234 - 237
  • [5] ARORA S, 1974, SYNTHESIS-STUTTGART, P801
  • [6] BAKER R, 1978, TETRAHEDRON LETT, P3575
  • [7] Synthesis of mono-, di-, and trisilyl-substituted alkenes via the hydrosilylation of methylenecyclopropanes catalyzed by Rh(I) complexes
    Bessmertnykh, AG
    Blinov, KA
    Grishin, YK
    Donskaya, NA
    Tveritinova, EV
    Yureva, NM
    Beletskaya, IP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) : 6069 - 6076
  • [8] PALLADIUM-CATALYZED ADDITION OF MALONATE TYPE COMPOUNDS TO ALLENES VIA A HYDROPALLADATION PROCESS
    BESSON, L
    GORE, J
    GAZES, B
    [J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3853 - 3856
  • [9] SYNTHESIS OF ALLYLIC AMINES THROUGH THE PALLADIUM-CATALYZED HYDROAMINATION OF ALLENES
    BESSON, L
    GORE, J
    GAZES, B
    [J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3857 - 3860
  • [10] OXIDATIVE ADDITION OF O-H BOND TO A METAL CENTER - SYNTHESIS AND CRYSTAL-STRUCTURE OF TRANS-(PHO)(H)PD(PCY3)2.PHOH
    BRAGA, D
    SABATINO, P
    DIBUGNO, C
    LEONI, P
    PASQUALI, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (03) : C46 - C48