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
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 13期
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
  • [21] Domino Cross Dehydrogenative Coupling of 2-Aryl Acetals with Ketones Using DDQ as Oxidant and Reactant Precursor
    Li Jiangsheng
    Cai Feifei
    Li Zhiwei
    Xue Yuan
    Cheng Chao
    Liu Weidong
    Cao Zhong
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (08) : 1699 - 1701
  • [22] Cross-Dehydrogenative-Coupling of Alkoxybenzenes with Toluenes: Copper(II) Halide Mediated Tandem Halo/Benzylation of Arenes
    Storr, Thomas E.
    Teskey, Christopher J.
    Greaney, Michael F.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (50) : 18169 - 18178
  • [23] DDQ-mediated Direct C(sp3)H Cyanation of Benzyl Ethers and 1,3-Diarylpropenes under Solvent- and Metal-free Conditions
    Kong, Shanshan
    Zhang, Lingqiong
    Dai, Xiaoli
    Tao, Lianzhi
    Xie, Chunsong
    Shi, Lei
    Wang, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) : 2453 - 2456
  • [24] Visible-light induced Cross-Dehydrogenative-Coupling (CDC) reactions of N-aryl tetrahydroisoquinolines under aerobic conditions
    Lin, Chao
    Li, Peiwu
    Wang, Lin
    TETRAHEDRON LETTERS, 2021, 73
  • [25] Photoinduced HCl-Mediated Cross-Dehydrogenative Coupling of Quinolines with Alcohols and Ethers
    Guo, Feixiang
    Guo, Yingchang
    Sun, Qianqian
    Zhang, Tao
    Wang, Yakun
    Fang, Lizhen
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (19): : 14204 - 14208
  • [26] Metal-free iodine-catalyzed direct cross-dehydrogenative coupling (CDC) between pyrazoles and thiols
    Yang, Daoshan
    Sun, Pengfei
    Wei, Wei
    Meng, Lingduan
    He, Lingchao
    Fang, Baokai
    Jiang, Wei
    Wang, Hua
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11): : 1457 - 1461
  • [27] The O2-Mediated Cross-Dehydrogenative Coupling: Rose Bengal-Catalyzed Direct Oxidative α-Acyloxylation of Ketones
    Zhu, Yunsheng
    Song, Shengjie
    Zheng, Lijun
    Li, Jianjun
    ORGANIC LETTERS, 2023, 25 (26) : 4918 - 4922
  • [28] Transition-metal-free direct cross-dehydrogenative coupling reactions of quinolinones with ethers
    Wang, Gang
    Wang, Jun-Tao
    Zhao, Bing
    Chen, Huan
    Zhang, Pan-Ke
    Han, Shu-Lei
    TETRAHEDRON LETTERS, 2020, 61 (04)
  • [29] Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines
    Dong, Jianyang
    Xia, Qing
    Lv, Xueli
    Yang, Changcun
    Song, Hongjian
    Liu, Yuxiu
    Wang, Qingmin
    ORGANIC LETTERS, 2018, 20 (18) : 5661 - 5665
  • [30] A visible light mediated, metal and oxidant free highly efficient cross dehydrogenative coupling (CDC) reaction between quinoxalin-2(1H)-ones and ethers
    Mane, Kishor D.
    Kamble, Rohit B.
    Suryavanshi, Gurunath
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (19) : 7403 - 7408
12345