SAMARIUM DIBROMIDE, AN EFFICIENT REAGENT FOR THE PINACOL COUPLING REACTIONS

被引：58
作者：
LEBRUN, A [1 ]
NAMY, JL [1 ]
KAGAN, HB [1 ]
机构：
[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,SYNTH ASYMETR LAB,CNRS,URA 1497,F-91405 ORSAY,FRANCE
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 14期
关键词：
D O I：
10.1016/S0040-4039(00)77601-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The preparation Of SmBr2 from Sm2O3 is described. This samarium (II) compound is a powerful one electron reductant able to very efficiently mediate pinacolic couplings. Cross Couplings are effective in some cases, for exam diol can be obtained from benzophenone and camphor. Intramolecular pinacolization of a diketone has also been performed.
引用
收藏
页码：2311 / 2314
页数：4
相关论文
共 15 条
  • [1] BARNIER JP, 1976, B SOC CHIM FR II-CH, P281
  • [2] THE STEREOCONTROLLED FORMATION OF CYCLIC VICINAL CIS-DIOLS VIA A SAMARIUM DIIODIDE PINACOL COUPLING OF DIALDEHYDES
    CHIARA, JL
    CABRI, W
    HANESSIAN, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (09) : 1125 - 1128
  • [3] MAGNESIUM-INDUCED AND TITANIUM-INDUCED REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS - EFFICIENT SYNTHESES OF PINACOLS AND ALKENES
    FURSTNER, A
    CSUK, R
    ROHRER, C
    WEIDMANN, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1729 - 1734
  • [4] DIVALENT LANTHANIDE DERIVATIVES IN ORGANIC-SYNTHESIS .1. MILD PREPARATION OF SMI2 AND YBI2 AND THEIR USE AS REDUCING OR COUPLING AGENTS
    GIRARD, P
    NAMY, JL
    KAGAN, HB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (08) : 2693 - 2698
  • [5] NUCLEOPHILIC-ADDITION OF LANTHANOID METAL UMPOLED DIARYL KETONES TO ELECTROPHILES
    HOU, ZM
    TAKAMINE, K
    AOKI, O
    SHIRAISHI, H
    FUJIWARA, Y
    TANIGUCHI, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) : 6077 - 6084
  • [6] REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS TO PINACOLS BY USING LOW-VALENT CERIUM
    IMAMOTO, T
    KUSUMOTO, T
    HATANAKA, Y
    YOKOYAMA, M
    [J]. TETRAHEDRON LETTERS, 1982, 23 (13) : 1353 - 1356
  • [7] KAN T, 1991, SYNLETT, P391
  • [8] LEBRUN A, UNPUB
  • [9] SYNTHESIS OF UNSYMMETRICAL OLEFINS BY TITANIUM(0) INDUCED MIXED CARBONYL COUPLING - SOME COMMENTS ON MECHANISM OF PINACOL REACTION
    MCMURRY, JE
    KREPSKI, LR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) : 3929 - 3930
  • [10] MOLANDER GA, 1989, J AM CHEM SOC, V111, P2132
12