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 [J].
Al-Masum, M ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3809-3810
[2]   The two component palladium catalyst system for intermolecular hydroamination of allenes [J].
AlMasum, M ;
Meguro, M ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 1997, 38 (34) :6071-6074
[3]   NICKEL-CATALYZED AND PALLADIUM-CATALYZED ADDITIONS OF NUCLEOPHILES TO CYCLIC 1,3-DIENES [J].
ANDELL, OS ;
BACKVALL, JE ;
MOBERG, C .
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 [J].
ARMBRUSTER, RW ;
MORGAN, MM ;
SCHMIDT, JL ;
LAU, CM ;
RILEY, RM ;
ZABROWSKI, DL ;
DIECK, HA .
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 [J].
Bessmertnykh, AG ;
Blinov, KA ;
Grishin, YK ;
Donskaya, NA ;
Tveritinova, EV ;
Yureva, NM ;
Beletskaya, IP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6069-6076
[8]   PALLADIUM-CATALYZED ADDITION OF MALONATE TYPE COMPOUNDS TO ALLENES VIA A HYDROPALLADATION PROCESS [J].
BESSON, L ;
GORE, J ;
GAZES, B .
TETRAHEDRON LETTERS, 1995, 36 (22) :3853-3856
[9]   SYNTHESIS OF ALLYLIC AMINES THROUGH THE PALLADIUM-CATALYZED HYDROAMINATION OF ALLENES [J].
BESSON, L ;
GORE, J ;
GAZES, B .
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 [J].
BRAGA, D ;
SABATINO, P ;
DIBUGNO, C ;
LEONI, P ;
PASQUALI, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (03) :C46-C48