GENERAL-SYNTHESIS OF (Z)-ALK-1-EN-1-YL ESTERS VIA RUTHENIUM-CATALYZED ANTI-MARKOVNIKOV TRANS-ADDITION OF CARBOXYLIC-ACIDS TO TERMINAL ALKYNES

被引:157
作者
DOUCET, H [1 ]
MARTINVACA, B [1 ]
BRUNEAU, C [1 ]
DIXNEUF, PH [1 ]
机构
[1] UNIV RENNES 1,CHIM COORDINAT ORGAN LAB,CNRS,URA 415,F-35042 RENNES,FRANCE
关键词
D O I
10.1021/jo00127a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct addition of carboxylic acids to terminal alkynes in the presence of catalytic amounts of (bis(diphenylphosphino)alkane)Ru(eta(3)-methallyl)(2) complexes provides a novel selective route to (Z)-alk-1-en-1-yl esters. This reaction involves an anti-Markovnikov and trans-addition to alkynes and gives access to a variety of new (Z)-alkene derivatives from hex-1-yne, phenylacetylene, and (trimethylsilyl)acetylene. The actual catalyst precursors are (bis(diphenylphosphino)alkane)Ru(eta(2)-carboxylate)(2) complexes formed in situ during the reaction.
引用
收藏
页码:7247 / 7255
页数:9
相关论文
共 98 条
  • [1] PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES
    ARCADI, A
    BURINI, A
    CACCHI, S
    DELMASTRO, M
    MARINELLI, F
    PIETRONI, BR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) : 976 - 982
  • [2] ENANTIOSELECTIVE HYDROFORMYLATION WITH THE CHIRAL BIDENTATE P,N-LIGAND 2-[1-(1S,2S,5R)-(-)MENTHOXYDIPHENYLPHOSPHINO]PYRIDINE CATIONIC RHODIUM(I) COMPLEXES
    ARENA, CG
    NICOLO, F
    DROMMI, D
    BRUNO, G
    FARAONE, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (19) : 2251 - 2252
  • [3] STEREOCHEMISTRY OF THE ACETOXYMERCURATION OF ALKYNES - A SYNTHESIS OF VINYL ACETATES
    BACH, RD
    WOODARD, RA
    ANDERSON, TJ
    GLICK, MD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) : 3707 - 3712
  • [4] ACTIVATION OF 1-ALKYNES AT TRIPODAL (POLYPHOSPHINE)RHODIUM SYSTEMS - REGIOSELECTIVE SYNTHESIS OF ENOL ESTERS FROM 1-ALKYNES AND CARBOXYLIC-ACIDS CATALYZED BY RHODIUM(I) MONOHYDRIDES
    BIANCHINI, C
    MELI, A
    PERUZZINI, M
    ZANOBINI, F
    BRUNEAU, C
    DIXNEUF, PH
    [J]. ORGANOMETALLICS, 1990, 9 (04) : 1155 - 1160
  • [5] BLANC PY, 1961, HELV CHIM ACTA, P1
  • [6] EASY ACCESS TO 5-(E)-ALKYNYLIDENE-TETRAHYDRO-2-FURANONES BY A PALLADIUM CATALYZED PROCESS
    BOUYSSI, D
    GORE, J
    BALME, G
    [J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2811 - 2814
  • [7] RUTHENIUM-CATALYZED ADDITIONS TO ALKYNES - SYNTHESIS OF ACTIVATED ESTERS AND THEIR USE IN ACYLATION REACTIONS
    BRUNEAU, C
    NEVEUX, M
    KABOUCHE, Z
    RUPPIN, C
    DIXNEUF, PH
    [J]. SYNLETT, 1991, (11) : 755 - 763
  • [8] REACTIONS OF ENOL ACETATES WITH THALLIUM(I) ACETATE-IODINE
    CAMBIE, RC
    HAYWARD, RC
    JURLINA, JL
    RUTLEDGE, PS
    WOODGATE, PD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (02): : 126 - 130
  • [9] ISOMERISATION OF PHENYLPROPARGYLIDENEMALONIC ACID TO GAMMA-BENZYLIDENE-ALPHA-CARBOXYBUTENOLIDE
    CASTANER, J
    PASCUAL, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1958, (NOV): : 3962 - 3964
  • [10] TRANSITION-METAL-CATALYZED CYCLIZATION OF ALKYNOIC ACIDS TO ALKYLIDENE LACTONES
    CHAN, DMT
    MARDER, TB
    MILSTEIN, D
    TAYLOR, NJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) : 6385 - 6388