General approach to the coupling of organoindium reagents with imines via copper catalysis

被引:48
作者
Black, DA [1 ]
Arndtsen, BA [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ol060277p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed three-component coupling of organoindium reagents with imines and acid chlorides is described. This mild carbon-carbon bond forming reaction requires only one-third of an equivalent of indium reagent to proceed in high yield, with the sole byproduct being indium trichloride. The reaction demonstrates broad generality, with aryl-, heteroaryl-, vinyl-, and alkylindiums, as well as functionalized imines and acid chlorides, all providing alpha-substituted amides or N-protected amines in a single step.
引用
收藏
页码:1991 / 1993
页数:3
相关论文
共 51 条
  • [1] Alonso F, 1997, RRD ORG CHEM, V1, P397
  • [2] [Anonymous], 1996, PALLADIUM REAGENTS C
  • [3] CARBOINDATION OF ALKYNES - REGIOSELECTIVE AND STEREOSELECTIVE ALLYLATION OF CARBON-CARBON TRIPLE BONDS OF ALKYNOLS BY ALLYLIC INDIUM REAGENTS
    ARAKI, S
    IMAI, A
    SHIMIZU, K
    YAMADA, M
    MORI, A
    BUTSUGAN, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) : 1841 - 1847
  • [4] Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents
    Araki, S
    Horie, T
    Kato, M
    Hirashita, T
    Yamamura, H
    Kawai, M
    [J]. TETRAHEDRON LETTERS, 1999, 40 (12) : 2331 - 2334
  • [5] Barbier P., 1899, CR HEBD ACAD SCI, V128, P110
  • [6] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS
    BASILE, T
    BOCOUM, A
    SAVOIA, D
    UMANIRONCHI, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7766 - 7773
  • [7] INDIUM-MEDIATED ALLYLATION OF ALDIMINES
    BEUCHET, P
    LEMARREC, N
    MOSSET, P
    [J]. TETRAHEDRON LETTERS, 1992, 33 (40) : 5959 - 5960
  • [8] Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes:: A multicomponent synthesis of α-substituted amides
    Black, DA
    Arndtsen, BA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 5133 - 5138
  • [9] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
    Bloch, R
    [J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
  • [10] BLOMBERG, 1993, BARBIER REACTION REL