Synthesis of Polysubstituted Furans via Copper-Mediated Annulation of Alkyl Ketones with α,β-Unsaturated Carboxylic Acids

被引：67
|
作者：
Yang, Yuzhu [1 ]
Yao, Jinzhong [1 ]
Zhang, Yuhong [1 ,2 ]
机构：
[1] Zhejiang Univ, ZJU NHU United R&D Ctr, Dept Chem, Hangzhou 310027, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 13期
关键词：
C-H BONDS; CATALYZED DECARBOXYLATIVE ARYLATION; ALPHA-OXOCARBOXYLIC ACIDS; BENZOIC-ACIDS; VERSATILE CATALYST; OLEFINATION; ACYLATION; FUNCTIONALIZATION; ALKENYLATION; STRATEGY;
D O I：
10.1021/ol400912v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel copper-mediated annulation of alkyl ketones with alpha,beta-unsaturated carboxylic acids has been accomplished. This reaction provides a facile and regio-defined method for the synthesis of 2,3,5-trisubstituted furans from simple chemical reagents.
引用
收藏
页码：3206 / 3209
页数：4
相关论文
共 50 条
  • [41] Copper-Mediated Aminoazidation, Aminohalogenation, and Aminothiocyanation of β,γ-Unsaturated Hydrazones: Synthesis of Versatile Functionalized Pyrazolines
    Wang, Li-Jing
    Ren, Pei-Xing
    Qi, Lin
    Chen, Manman
    Lu, Yan-Lei
    Zhao, Jing-Ye
    Liu, Rui
    Chen, Jia-Min
    Li, Wei
    ORGANIC LETTERS, 2018, 20 (15) : 4411 - 4415
  • [42] Total Synthesis of (±)-Marinopyrrole A via Copper-Mediated N-Arylation
    Kanakis, Argyrios A.
    Sarli, Vasiliki
    ORGANIC LETTERS, 2010, 12 (21) : 4872 - 4875
  • [43] Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction
    Fu, Xue-wen
    Pu, Wen-chen
    Zhang, Guo-lin
    Wang, Chun
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (11) : 8147 - 8158
  • [44] Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids
    Mossine, Andrew V.
    Brooks, Allen F.
    Makaravage, Katarina J.
    Miller, Jason M.
    Ichiishi, Naoko
    Sanford, Melanie S.
    Scott, Peter J. H.
    ORGANIC LETTERS, 2015, 17 (23) : 5780 - 5783
  • [45] An efficient process for the synthesis of γ-arylbutanals via copper-mediated Grignard coupling
    Monte, WT
    Lindbeck, AC
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) : 267 - 269
  • [46] Copper-Mediated Cascade Synthesis of Diaryl Sulfones via the Sandmeyer Reaction
    Yang, Xiaobo
    Shi, Liangliang
    Fu, Hua
    SYNLETT, 2014, 25 (06) : 847 - 852
  • [47] DBU-Mediated Construction of 1,3,5-Trisubstituted Benzenes via Annulation of α,β-Unsaturated Carboxylic Acids and α-Cyano-β-methylenones
    Zhang, Chun-Lin
    Zhang, Zhao-Fei
    Xia, Zi-Hao
    Han, You-Feng
    Ye, Song
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12507 - 12513
  • [48] Development of copper-mediated allylation of γ-activated-α,β-unsaturated lactam toward peptide mimetic synthesis
    Sasaki, Yoshikazu
    Yamaguchi, Keiko
    Tsuji, Takashi
    Shigenaga, Akira
    Fujii, Nobutaka
    Otaka, Akira
    TETRAHEDRON LETTERS, 2007, 48 (18) : 3221 - 3224
  • [49] Synthesis of polysubstituted pyridazines via Cu-mediated C(sp3)-C(sp3) coupling/annulation of saturated ketones with acylhydrazones
    Zhou, Honggui
    Li, Zhefeng
    Chen, Juehong
    Zhou, Si
    Wang, Xinyu
    Zhang, Linwei
    Chen, Jiuxi
    Lv, Ningning
    CHEMICAL COMMUNICATIONS, 2024, 60 (71) : 9546 - 9549
  • [50] Synthesis of Vinyl Trifluoromethyl Thioethers via Copper-Mediated Trifluoromethylthiolation of Vinyl Bromides
    Huang, Yangjie
    Ding, Jianping
    Wu, Chuyi
    Zheng, Huidong
    Wen, Zhiqiang
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05): : 2912 - 2917
12345