THE USE OF ORTHO-CHELATING ARENETHIOLATE NONTRANSFERABLE GROUPS IN THE COPPER(I) CATALYZED SELECTIVE ALPHA-SUBSTITUTION OR GAMMA-SUBSTITUTION OF ACYCLIC ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS

被引:35
作者
VANKLAVEREN, M
PERSSON, ESM
GROVE, DM
BACKVALL, JE
VANKOTEN, G
机构
[1] UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
[2] UNIV UTRECHT,DEBYE RES INST,DEPT MET MEDIATED SYNTH,3584 CH UTRECHT,NETHERLANDS
关键词
D O I
10.1016/S0040-4039(00)78222-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ortho-amino arenethiolatocopper(I) compounds are excellent catalysts for the cross-coupling reaction of Grignard reagents with acyclic allylic substrates. For example, reaction of n-BuMgI with geranyl acetate in Et(2)O at 0 degrees C yields quantitatively the gamma substitution product, whereas the same reaction in THF at -30 degrees C affords selectively the a substitution product.
引用
收藏
页码:5931 / 5934
页数:4
相关论文
共 20 条
  • [1] ARAI M, 1992, TETRAHEDRON, V48, P5709
  • [2] BACKVALL JE, 1990, J AM CHEM SOC, V112, P6615
  • [3] BACKVALL JE, 1994, IN PRESS J ORG CHEM
  • [4] SUBSTITUTION OF ALLYLIC SULFIDES OF BENZOTHIAZOLE-2-THIOL WITH ORGANOMAGNESIUM COMPOUNDS IN THE PRESENCE OF COPPER(I) IODIDE - REGIOSELECTIVE SYNTHESIS OF OLEFINS
    BARSANTI, P
    CALO, V
    LOPEZ, L
    MARCHESE, G
    NASO, F
    PESCE, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (24) : 1085 - 1086
  • [5] GOERING HL, 1991, J ORG CHEM, V56, P2563
  • [6] 1,6-ADDITION OF ORGANOLITHIUM COMPOUNDS TO ACCEPTOR-SUBSTITUTED ENYNES CATALYZED BY A COPPER(I) ARENETHIOLATE
    HAUBRICH, A
    VANKLAVEREN, M
    VANKOTEN, G
    HANDKE, G
    KRAUSE, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5849 - 5852
  • [7] Knotter D. M., 1989, ANGEW CHEM, V101, P351
  • [8] SYNTHESIS AND PROPERTIES OF TRIMERIC ORTHO-CHELATED (ARENETHIOLATO)COPPER(I) COMPLEXES
    KNOTTER, DM
    VANMAANEN, HL
    GROVE, DM
    SPEK, AL
    VANKOTEN, G
    [J]. INORGANIC CHEMISTRY, 1991, 30 (17) : 3309 - 3317
  • [9] A NEW CLASS OF ORGANOCOPPER AND ORGANOCUPRATE COMPOUNDS DERIVED FROM COPPER(I) ARENETHIOLATES
    KNOTTER, DM
    GROVE, DM
    SMEETS, WJJ
    SPEK, AL
    VANKOTEN, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) : 3400 - 3410
  • [10] SYNTHESIS AND MOLECULAR-STRUCTURE OF COPPER(I) AND ORGANOZINC(II) ARENETHIOLATES WITH CHELATING AMINO AND ETHER GROUPS - X-RAY STRUCTURE OF [CUSC6H4(CH2N(ME)CH2CH2OME)-2]4 AND [ZN(ME)(SC6H4((R)-CH(ME)NME2)-2)]2
    KNOTTER, DM
    JANSSEN, MD
    GROVE, DM
    SMEETS, WJJ
    HORN, E
    SPEK, AL
    VANKOTEN, G
    [J]. INORGANIC CHEMISTRY, 1991, 30 (23) : 4361 - 4366