P(MeNMCH2CH2)3N:: an effective catalyst for trimethylsilycyanation of aldehydes and ketones

被引:59
作者
Wang, ZG [1 ]
Fetterly, B [1 ]
Verkade, JG [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
基金
美国国家科学基金会;
关键词
aminophosphine catalyst; bicyclic phosphazane; ketone trimethylsilylcyanation; aldehyde trimethysilylcyanation; hypercoordinate silicon; transannulation;
D O I
10.1016/S0022-328X(01)01436-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The title non-ionic phosphazane base promotes the trimethylsilycyanation of aryl and alkyl aldehydes and ketones in moderate to high yields at room temperature. Si-29-NMR spectral evidence for the intermediacy of a phosphazane phosphorus-silicon adduct is presented. (C) 2002 Published by Elsevier Science B.V.
引用
收藏
页码:161 / 166
页数:6
相关论文
共 74 条
  • [1] ABELE E, 2000, CHEM HETEROCYCL COMP, V35, P943
  • [2] P(CH3NCH2CH2)(3)N: A nonionic superbase for efficient dehydrohalogenation
    Arumugam, S
    Verkade, JG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4827 - 4828
  • [3] Use of the nonionic superbase P(MeNCH2CH2)3N in the selective monoalkylation of active-methylene compounds
    Arumugam, S
    McLeod, D
    Verkade, JG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) : 3677 - 3679
  • [4] Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes
    Aspinall, HC
    Greeves, N
    Smith, PM
    [J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1763 - 1766
  • [5] Asymmetric trimethylsilylcyanation of benzaldehyde catalyzed by (salen)Ti(IV) complexes derived from (R)- and/or (S)-4-hydroxy-5-formyl[2.2]paracyclophane and diamines
    Belokon, Y
    Moscalenko, M
    Ikonnikov, N
    Yashkina, L
    Antonov, D
    Vorontsov, E
    Rozenberg, V
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3245 - 3250
  • [6] The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex
    Belokon, YN
    Green, B
    Ikonnikov, NS
    North, M
    Tararov, VI
    [J]. TETRAHEDRON LETTERS, 1999, 40 (46) : 8147 - 8150
  • [7] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF ALDEHYDES
    BOLM, C
    MULLER, P
    [J]. TETRAHEDRON LETTERS, 1995, 36 (10) : 1625 - 1628
  • [8] 5-CO-ORDINATED SILICON-COMPOUNDS - GEOMETRY OF FORMATION BY INTRAMOLECULAR COORDINATION - CRYSTAL-STRUCTURE OF 2-(DIMETHYLAMINOMETHYL)PHENYL-1-NAPHTHYLSILANE
    BOYER, J
    BRELIERE, C
    CARRE, F
    CORRIU, RJP
    KPOTON, A
    POIRIER, M
    ROYO, G
    YOUNG, JC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1989, (01): : 43 - 51
  • [9] Enantioselective trimethylsilylcyanation of aromatic aldehydes catalyzed by titanium alkoxide-chiral o-hydroxyarylphosphine oxides complexes
    Brunel, JM
    Legrand, O
    Buono, G
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (10) : 1979 - 1984
  • [10] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
    CHUIT, C
    CORRIU, RJP
    REYE, C
    YOUNG, JC
    [J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1371 - 1448