CATALYTIC ADDITION OF AROMATIC C-H BONDS TO ACETYLENES

被引:192
作者
KAKIUCHI, F [1 ]
YAMAMOTO, Y [1 ]
CHATANI, N [1 ]
MURAI, S [1 ]
机构
[1] OSAKA UNIV,FAC ENGN,DEPT APPL CHEM,SUITA,OSAKA 565,JAPAN
关键词
D O I
10.1246/cl.1995.681
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of alpha-tetralone with various internal acetylenes can be catalyzed by Ru(H)(2)(CO)(PPh(3))(3) and gives 1:1 addition products. Symmetrically substituted dialkyl- and diaryiacetylenes gave an E/Z mixture of 1:1 coupling products in good yields. 1-Phenyl-1-butyne afforded all four possible regio- and stereoisomers. 1-Trimethylsilyl-1-propyne gave only E-isomer with C-C bond formation exclusively at the carbon atom substituted with the silyl group. Other internal acetylenes having a trimethylsilyl group also proceeded regioselectively although mixtures of stereoisomers were obtained.
引用
收藏
页码:681 / 682
页数:2
相关论文
共 33 条
  • [11] REACTIONS OF BENZENES WITH ACETYLENES CATALYZED BY RHODIUM CARBONYL UNDER CARBON-MONOXIDE
    HONG, P
    CHO, BR
    YAMAZAKI, H
    [J]. CHEMISTRY LETTERS, 1979, (04) : 339 - 342
  • [12] ITO K, 1983, CHEM LETT, P499
  • [13] SYNTHESIS AND REACTIONS OF ETA-5-CYCLOPENTADIENYLBIS(ETHENE)COBALT
    JONAS, K
    DEFFENSE, E
    HABERMANN, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (09): : 716 - 717
  • [14] CATALYTIC ADDITION OF AROMATIC CARBON-HYDROGEN BONDS TO OLEFINS WITH THE AID OF RUTHENIUM COMPLEXES
    KAKIUCHI, F
    SEKINE, S
    TANAKA, Y
    KAMATANI, A
    SONODA, M
    CHATANI, N
    MURAI, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (01) : 62 - 83
  • [15] KAKIUCHI F, 1995, IN PRESS CHEM LETT, V8, P679
  • [16] CATALYTIC SYNTHESIS OF VINYL CARBAMATES FROM CARBON-DIOXIDE AND ALKYNES WITH RUTHENIUM COMPLEXES
    MAHE, R
    SASAKI, Y
    BRUNEAU, C
    DIXNEUF, PH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1518 - 1523
  • [17] C-H RATHER THAN O-H ACTIVATION - SYNTHESIS AND MOLECULAR-STRUCTURE OF A CATIONIC CIS-HYDRIDO-SIGMA-ACETYLIDE COMPLEX OF RHODIUM
    MARDER, TB
    ZARGARIAN, D
    CALABRESE, JC
    HERSKOVITZ, TH
    MILSTEIN, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) : 1484 - 1485
  • [18] MECHANISTIC STUDY ON CP-MEDIATED AND CP-ASTERISK-RU+-MEDIATED CYCLOADDITION BETWEEN CONJUGATED DIENES AND ACETYLENE
    MASUDA, K
    OHKITA, H
    KURUMATANI, S
    ITOH, K
    [J]. ORGANOMETALLICS, 1993, 12 (06) : 2221 - 2226
  • [19] RUTHENIUM COMPLEX-CATALYZED HIGHLY SELECTIVE CODIMERIZATION OF ACETYLENES AND ALKENES
    MITSUDO, T
    ZHANG, SW
    NAGAO, M
    WATANABE, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (08) : 598 - 599
  • [20] EFFICIENT CATALYTIC ADDITION OF AROMATIC CARBON-HYDROGEN BONDS TO OLEFINS
    MURAI, S
    KAKIUCHI, F
    SEKINE, S
    TANAKA, Y
    KAMATANI, A
    SONODA, M
    CHATANI, N
    [J]. NATURE, 1993, 366 (6455) : 529 - 531