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 50 条
  • [1] DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones
    Zhang, Yuhua
    Li, Chao-Jun
    Journal of the American Chemical Society, 2006, 128 (13): : 4242 - 4243
  • [2] DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates
    Cheng, Ming-Xing
    Lei, Jing-Wei
    Xie, Cai-Xia
    SYNLETT, 2019, 30 (01) : 114 - 118
  • [3] Cross-Dehydrogenative-Coupling (CDC) Reaction
    Guo Xingwei
    Li Zhiping
    Li Chaojun
    PROGRESS IN CHEMISTRY, 2010, 22 (07) : 1434 - 1441
  • [4] Biomimetic Total Synthesis of Clavicipitic Acid: A DDQ-Mediated Intramolecular Cross-Dehydrogenative Coupling Approach
    Chiu, Kuei-Wei
    Tseng, Yu-Hsun
    Li, Ying-Xin
    Chein, Rong-Jie
    ORGANIC LETTERS, 2023, 25 (19) : 3456 - 3460
  • [5] Highly efficient cross-dehydrogenative-coupling between ethers and active methylene compounds
    Zhang, YH
    Li, CJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) : 1949 - 1952
  • [6] Copper-catalyzed dehydrogenative cross-coupling reaction between unactivated ethers and simple ketones mediated by pyrrolidine
    Huang, Xing-Fen
    Zhu, Zhi-Qiang
    Huang, Zhi-Zhen
    TETRAHEDRON, 2013, 69 (40) : 8579 - 8582
  • [7] DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids
    Bhunia, Subhajit
    Ghosh, Santanu
    Dey, Dhananjay
    Bisai, Alakesh
    ORGANIC LETTERS, 2013, 15 (10) : 2426 - 2429
  • [8] Iron-mediated cross dehydrogenative coupling (CDC) of terminal alkynes with benzylic ethers and alkanes
    Xiang Shi-Kai
    Zhang Bo
    Zhang Li-He
    Cui YuXin
    Jiao Ning
    SCIENCE CHINA-CHEMISTRY, 2012, 55 (01) : 50 - 54
  • [9] Iron-mediated cross dehydrogenative coupling (CDC) of terminal alkynes with benzylic ethers and alkanes
    Shi-Kai Xiang
    Bo Zhang
    Li-He Zhang
    YuXin Cui
    Ning Jiao
    Science China Chemistry, 2012, 55 : 50 - 54
  • [10] Iron-mediated cross dehydrogenative coupling(CDC) of terminal alkynes with benzylic ethers and alkanes
    XIANG ShiKaiZHANG BoZHANG LiHeCUI YuXin JIAO Ning State Key Laboratory of Natural and Biomimetic Drugs
    School of Pharmaceutical SciencesPeking UniversityBeijing China Shanghai Key Laboratory of Green Chemistry and Chemical ProcessesDepartment of ChemistryEast China Normal UniversityShanghai China
    Science China(Chemistry), 2012, 55 (01) : 50 - 54