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
  • [31] Cross-Dehydrogenative Coupling between Enamino Esters and Ketones: Synthesis of Tetrasubstituted Pyrroles
    Zhao, Miao
    Wang, Fen
    Li, Xingwei
    ORGANIC LETTERS, 2012, 14 (06) : 1412 - 1415
  • [32] Highly Chemoselective and Regioselective Dehydrogenative Cross-Coupling Reaction between Pyridines and Ethers
    Salman, Muhammad
    Huang, Xing-Fen
    Huang, Zhi-Zhen
    SYNLETT, 2015, 26 (10) : 1391 - 1394
  • [33] Metal-Free Visible-Light-Induced C-H/C-H Cross-Dehydrogenative-Coupling of Quinoxalin-2(H)-ones with Simple Ethers
    Wei, Wei
    Wang, Leilei
    Yue, Huilan
    Bao, Pengli
    Liu, Weiwei
    Hu, Changsong
    Yang, Daoshan
    Wang, Hua
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (12): : 17252 - 17257
  • [34] Direct Cα-heteroarylation of structurally diverse ethers via a mild N-hydroxysuccinimide mediated cross-dehydrogenative coupling reaction
    Liu, Shihui
    Liu, Aoxia
    Zhang, Yongqiang
    Wang, Wei
    CHEMICAL SCIENCE, 2017, 8 (05) : 4044 - 4050
  • [35] A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation
    Feizpour, Fahimeh
    Jafarpour, Maasoumeh
    Rezaeifard, Abdolreza
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (02) : 807 - 811
  • [36] Recent advances in rhodium-catalysed cross-dehydrogenative-coupling between two C(sp2)-H bonds
    Tsang, Yi Ling
    Choy, Pui Ying
    Leung, Man Pan
    He, Xinwei
    Kwong, Fuk Yee
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07) : 1992 - 2012
  • [37] Visible-light-mediated photocatalytic cross-coupling of acetenyl ketones with benzyl trifluoroborate
    Zhang, Lingchun
    Chu, Yanle
    Ma, Peizhi
    Zhao, Shujuan
    Li, Qiaoyan
    Chen, Boya
    Hong, Xuejiao
    Sun, Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (06) : 1073 - 1077
  • [38] Silver-Catalyzed Cross Dehydrogenative Coupling between Heteroarenes and Cyclic Ethers under Mild Conditions
    Zhou, Zhong
    Wu, Yunli
    Yang, Peng
    Deng, Shijun
    Zhang, Qian
    Li, Dong
    CHEMISTRYSELECT, 2021, 6 (11): : 2770 - 2773
  • [39] Tetrabutylammonium Iodide-Catalyzed Phosphorylation of Benzyl C-H Bonds via a Cross-Dehydrogenative Coupling (CDC) Reaction
    Xu, Jian
    Zhang, Pengbo
    Li, Xueqin
    Gao, Yuzhen
    Wu, Ju
    Tang, Guo
    Zhao, Yufen
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) : 3331 - 3335
  • [40] A Concise, Metal-Free Approach to the Synthesis of Oxime Ethers from Cross-Dehydrogenative-Coupling of sp3 C-H Bonds with Oximes
    Jin, Jun
    Li, Yan
    Wang, Zhi-jing
    Qian, Wei-xing
    Bao, Wei-liang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (07) : 1235 - 1238
12345