DDQ-mediated direct Cross-Dehydrogenative-Coupling (CDC) between benzyl ethers and simple ketones

被引:383
作者
Zhang, YH
Li, CJ [1 ]
机构
[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ja060050p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A direct Cross-Dehydrogenative-Coupling (CDC) between benzyl ethers and simple ketones was developed without using any metal catalyst. By using DDQ, various benzyl ethers and simples ketones were coupled together directly to form β-alkoxyl ketones efficiently. A mechanism in which the DDQ serves the double roles of an oxidizing agent and an organomediator was proposed. Copyright © 2006 American Chemical Society.
引用
收藏
页码:4242 / 4243
页数:2
相关论文
共 39 条
  • [1] Anastas P. T., 1998, GREEN CHEM THEORY PR
  • [2] SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION
    ARNDTSEN, BA
    BERGMAN, RG
    MOBLEY, TA
    PETERSON, TH
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) : 154 - 162
  • [3] Oxidative synthesis of cyclic acyl aminals through carbon-carbon σ-bond activation
    Aubele, DL
    Floreancig, PE
    [J]. ORGANIC LETTERS, 2002, 4 (20) : 3443 - 3446
  • [4] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [5] BRAUDE EA, 1956, J CHEM SOC, P3037
  • [6] Buckle D. R., 1995, ENCY REAGENTS ORGANI, V3, P1699
  • [7] CACCHI S, 1978, SYNTHESIS-STUTTGART, P848
  • [8] A new and versatile allylic alcohol anion and acyl β-anion equivalent for three-carbon homologations
    Caputo, R
    Guaragna, A
    Palumbo, G
    Pedatella, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) : 9369 - 9371
  • [9] Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes
    Chatani, N
    Asaumi, T
    Yorimitsu, S
    Ikeda, T
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) : 10935 - 10941
  • [10] An oxidative Prins cyclization methodology
    Chen, CF
    Mariano, PS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3252 - 3254