Catalytic and metal-free intramolecular hydroalkoxylation of alkynes

被引:4
|
作者
Jean, Alexandre [1 ,2 ]
Rouden, Jacques [1 ]
Maddaluno, Jacques [2 ]
De Paolis, Michael [2 ]
Blanchet, Jerome [1 ]
机构
[1] Normandie Univ, CNRS, UMR 6507 & FR 3038, ENSICAEN,UNICAEN,Lab LCMT, F-14000 Caen, France
[2] Normandie Univ, CNRS, UMR 6014 & FR 3038, UNIROUEN,INSA Rouen,Lab COBRA, F-76000 Rouen, France
关键词
Hydroalkoxylation; Cyclization; Alkynes; Enol ether; Microwave-assisted synthesis; ENOL ETHERS; CYCLIZATION; ALCOHOLS; SCOPE; ALKYNYLPHENOLS; HYDROAMINATION; DERIVATIVES; MECHANISM; ANALOGS; ROUTE;
D O I
10.1016/j.tetlet.2019.01.020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzyltrimethylammonium hydroxide act as an efficient metal-free catalyst for the intramolecular hydroalkoxylation of alkynes. Notably, the use of microwave irradiation allowed reaction to operate in only two minutes. Under optimized reaction conditions, linear alkynes bearing aryl and heteroaryl substituents were successfully cyclized with good level of stereoselectivity. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:534 / 537
页数:4
相关论文
共 50 条
  • [1] Metal-Free Intramolecular Hydroalkoxylation of Alkyne: Recent Advances
    Nanda, Santosh K.
    [J]. CHEMISTRYSELECT, 2021, 6 (33): : 8511 - 8526
  • [2] Metal-free intramolecular hydroarylation of alkynes
    Zhang, Chaofeng
    Lv, Songkui
    Wang, Yanru
    Zhang, Jingyi
    Wang, Xiao-Na
    Chang, Junbiao
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (05) : 1300 - 1307
  • [3] A metal-free catalytic intramolecular hydrosilylation
    Steinberger, HU
    Bauch, C
    Müller, T
    Auner, N
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2003, 81 (11) : 1223 - 1227
  • [4] Metal-free hydroalkoxylation of ynesulfonamides with alcohols
    Wang, Hanhan
    Hu, Mengjun
    Wang, Xiao-Na
    Chang, Junbiao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (16) : 3408 - 3412
  • [5] Metal-free hydroalkoxylation of ynesulfonamides with esters
    Gao, Erhui
    Peng, Cheng
    Zhang, Jingyi
    Wang, Xiao-Na
    Chang, Junbiao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (10) : 2182 - 2185
  • [6] Bronsted Acid/Silane Catalytic System for Intramolecular Hydroalkoxylation and Hydroamination of Unactivated Alkynes
    Shibuya, Masatoshi
    Fujita, Shoji
    Abe, Masanori
    Yamamoto, Yoshihiko
    [J]. ACS CATALYSIS, 2017, 7 (04): : 2848 - 2852
  • [7] Metal-free intermolecular aminoarylation of alkynes
    Rabet, Pauline
    Boyd, Scott
    Greaney, Michael
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [8] Metal-Free Intermolecular Aminoarylation of Alkynes
    Rabet, Pauline T. G.
    Boyd, Scott
    Greaney, Michael F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4183 - 4186
  • [9] Metal-Free Intramolecular Aminophosphination of Allenes
    Yang, Zhantao
    Sun, Zhenzhen
    Zhu, Ningning
    Li, Wenyan
    Han, Meng
    Qiao, Yan
    Yang, Chun-Hua
    Chang, Junbiao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23): : 15686 - 15692
  • [10] Visible-light induced metal-free intramolecular reductive cyclisations of ketones with alkynes and allenes
    Tang, Nana
    Zachmann, Raphael J.
    Xie, Hui
    Zheng, Jun
    Breit, Bernhard
    [J]. CHEMICAL COMMUNICATIONS, 2023, 59 (15) : 2122 - 2125