Pyridine and phosphine reactions with [CPh3][B(C6F5)4]

被引:63
作者
Cabrera, Lourdes [1 ]
Welch, Gregory C. [1 ]
Masuda, Jason D. [1 ]
Wei, Pingrong [1 ]
Stephan, Douglas W. [1 ]
机构
[1] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
trityl borate; Lewis acid-base interaction; nucleophilic aromatic substitution;
D O I
10.1016/j.ica.2006.02.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Trityl borate salts [4-RPyCPh3][B(C6F5)(4)] (R = H 1, Bu-t 2, Et 3, NMe2 4) and [R3PCPh3][B(C6F5)(4)] (R = Me 5, Bu-n 6, Ph[1] 7, p-MeC6H4 8) are readily prepared via equimolar reaction of the appropriate pyridine or phosphine and trityl borate [CPh3][B(C6F5)(4)]. The analogous reactions of (PPr3)-Pr-i affords the product [(p-(Pr3P)-Pr-i-C6H4)Ph2CH][B(C6F5)(4)] (9) while the corresponding reactions of Cy3P and (Bu3P)-Bu-t gave the cyclohexadienyl derivatives [(p-R3PC6H5)CPh2][B(C6F5)(4)] (R = Cy 10, Bu-t 11). X-ray structures of 5 and 9 are reported. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:3066 / 3071
页数:6
相关论文
共 21 条
  • [1] BIDAN G, 1978, TETRAHEDRON LETT, V28, P2499
  • [2] Solution and solid-state characteristics of imine adducts with tris(pentafluorophenyl)borane
    Blackwell, JM
    Piers, WE
    Parvez, M
    McDonald, R
    [J]. ORGANOMETALLICS, 2002, 21 (07) : 1400 - 1407
  • [3] BRIEGLEB G, 1963, ANGEW CHEM INT EDIT, P2
  • [4] X-RAY SCATTERING FACTORS COMPUTED FROM NUMERICAL HARTREE-FOCK WAVE FUNCTIONS
    CROMER, DT
    MANN, JB
    [J]. ACTA CRYSTALLOGRAPHICA SECTION A-CRYSTAL PHYSICS DIFFRACTION THEORETICAL AND GENERAL CRYSTALLOGRAPHY, 1968, A 24 : 321 - &
  • [5] HYDRIDE TRANSFER . REACTIONS OF TRIPHENYLCARBONIUM FLUOROBORATE AND TRIPHENYLMETHYL BROMIDE WITH TERTIARY AMINES
    DAMICO, R
    BROADDUS, CD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (05) : 1607 - &
  • [6] B(C6F5)3-catalyzed formation of B-P bonds by dehydrocoupling of phosphine-boranes
    Denis, JM
    Forintos, H
    Szelke, H
    Toupet, L
    Pham, TN
    Madec, PJ
    Gaumont, AC
    [J]. CHEMICAL COMMUNICATIONS, 2003, (01) : 54 - 55
  • [7] DOERRER LH, 1998, DALTON T, P3941
  • [8] Triphenylmethyl tris(p-methoxyphenyl)phosphonium cation:: a structurally characterized phosphonium analog of hexaphenylethane
    Fang, XG
    Scott, BL
    John, KD
    Kubas, GJ
    Watkin, JG
    [J]. NEW JOURNAL OF CHEMISTRY, 2000, 24 (10) : 831 - 833
  • [9] Synthesis and reactivity of (C6F5)3B-N-heterocycle complexes.: 1.: Generation of highly acidic sp3 carbons in pyrroles and indoles
    Guidotti, S
    Camurati, I
    Focante, F
    Angellini, L
    Moscardi, G
    Resconi, L
    Leardini, R
    Nanni, D
    Mercandelli, P
    Sironi, A
    Beringhelli, T
    Maggioni, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) : 5445 - 5465
  • [10] HOFFMANN H, 1966, CHEM BER, V99, P134