Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C-O bond

被引:43
|
作者
Chen, Jing [1 ,2 ]
Chen, Chao [1 ]
Chen, Junjie [1 ]
Wang, Guohua [1 ]
Qu, Hongmei [2 ]
机构
[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
[2] Tianjin Univ, Sch Chem Engn & Technol, Dept Pharmaceut Engn, Key Lab Syst Bioengn,Minist Educ, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
METAL-FREE SYNTHESIS; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CASCADE ANNULATION; TETRAHYDROFURANS; CARBOETHERIFICATION; HETEROCYCLES; DERIVATIVES; ALKENES; ACETOGENINS;
D O I
10.1039/c4cc08363f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Cu-catalyzed intramolecular aryl-etherification reaction of alkoxyl alkynes with diaryliodonium salts is realized. The reactions proceed smoothly to produce valuable oxo-heterocycles with readily available linear starting materials via cleavage of a stable C-O bond.
引用
收藏
页码:1356 / 1359
页数:4
相关论文
共 50 条
  • [1] A Mild Ni/Cu-Catalyzed Silylation via C-O Cleavage
    Zarate, Cayetana
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (06) : 2236 - 2239
  • [2] Cu-catalyzed coupling of unactivated tertiary alkyl alcohols with thiols via C-O bond cleavage
    Xu, Bing
    Ye, Yang
    Lin, Ying
    Bai, Renren
    Ye, Xiang-Yang
    Xie, Tian
    TETRAHEDRON LETTERS, 2022, 89
  • [3] Synthesis of Quinoline Derivatives via Cu-Catalyzed Cascade Annulation of Heterocumulenes, Alkynes, and Diaryliodonium Salts
    Chi, Yen
    Yan, Haihan
    Zhang, Wen-Xiong
    Xi, Zhenfeng
    ORGANIC LETTERS, 2017, 19 (10) : 2694 - 2697
  • [4] Cu-Catalyzed Arylcarbocyclization of Alkynes with Diaryliodonium Salts through C-C Bond Formation on Inert C(sp3)-H Bond
    Peng, Jing
    Chen, Chao
    Chen, Junjie
    Su, Xiang
    Xi, Chanjuan
    Chen, Hui
    ORGANIC LETTERS, 2014, 16 (14) : 3776 - 3779
  • [5] Ni-Catalyzed Stannylation of Aryl Esters via C-O Bond Cleavage
    Gu, Yiting
    Martin, Ruben
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) : 3187 - 3190
  • [6] Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage
    Zhu, Zhaodong
    Gong, Yuxin
    Tong, Weiqi
    Xue, Weichao
    Gong, Hegui
    ORGANIC LETTERS, 2021, 23 (06) : 2158 - 2163
  • [7] Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage
    Yue, Huifeng
    Guo, Lin
    Liu, Xiangqian
    Rueping, Magnus
    ORGANIC LETTERS, 2017, 19 (07) : 1788 - 1791
  • [8] Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation
    Yoon, Hyung
    Galls, Alexandra
    Rozema, Soren D.
    Miller, Scott J.
    ORGANIC LETTERS, 2022, 24 (02) : 762 - 766
  • [9] Iridium(III)-Catalyzed Sequential C(2)-Arylation and Intramolecular C-O Bond Formation from Azulenecarboxylic Acids and Diaryliodonium Salts Access to Azulenofuranones
    Maeng, Chanyoung
    Seo, Hyung Jin
    Jeong, Haneal
    Lee, Kyungsup
    Noh, Hee Chan
    Lee, Phil Ho
    ORGANIC LETTERS, 2020, 22 (18) : 7267 - 7272
  • [10] Nickel-Catalyzed Alkynylation of Anisoles via C-O Bond Cleavage
    Tobisu, Mamoru
    Takahira, Tsuyoshi
    Ohtsuki, Akimichi
    Chatani, Naoto
    ORGANIC LETTERS, 2015, 17 (03) : 680 - 683