Silver-catalyzed oxidative alkylation/alkynylation of 1,4-enynyl-3-ols with alkylbromides through radical 1,2-alkynyl migration

被引:0
|
作者
Chen, De [1 ]
Zhang, Nianqi [1 ]
Liang, Qiuju [2 ,3 ]
Deng, Wei [1 ]
Xiao, Zhiyi [2 ]
Dong, Wanrong [1 ]
Xiang, Jiannan [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr, Minist Educ, Changsha 410082, Hunan, Peoples R China
[2] Wujo High Tech Mat Co Ltd, Hunan Engn Technol Ctr Photog Mat 2022TP2027, Loudi 417000, Hunan, Peoples R China
[3] China Tobacco Hunan Ind Co Ltd, Technol Ctr, Laodong Mid Rd 426, Changsha 410014, Hunan, Peoples R China
关键词
12-Alkynyl migration; Silver-catalysis; 1,4-Enynyl-3-ols; Alkylbrmodes; Alkynylation/alkylation; ALLYLIC ALCOHOLS; ALKENES; FUNCTIONALIZATION; DIFUNCTIONALIZATION; CARBON;
D O I
10.1016/j.catcom.2023.106824
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this study, we have described a novel reaction between 1,4-enynyl-3-ols and alkyl bromides. The reaction was carried out in the presence of Ag2O, following a free radical 1,2-alkynyl migration pathway, which was confirmed through control experiments. This methodology offers several advantages, including high efficiency and a wide range of applicable substrates.
引用
收藏
页数:5
相关论文
共 18 条
  • [1] Oxidative alkylation/alkynylation of terminal alkenes via alkylaldehyde decarbonylation and 1,2-alkynyl migration
    Zhang, Jia-Jia
    Chen, De
    Qin, Yi-Qun
    Deng, Wei
    Luo, Yong-Yue
    Xiang, Jian-Nan
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (14) : 3154 - 3158
  • [2] Cyanoalkylation/alkynylation of allylic alcohol through intramolecular radical 1,2-alkynyl migration
    Jin, Shengnan
    Chen, Fan
    Qian, Pengcheng
    Cheng, Jiang
    [J]. Organic and Biomolecular Chemistry, 2021, 19 (11): : 2416 - 2419
  • [3] Cyanoalkylation/alkynylation of allylic alcohol through intramolecular radical 1,2-alkynyl migration
    Jin, Shengnan
    Chen, Fan
    Qian, Pengcheng
    Cheng, Jiang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (11) : 2416 - 2419
  • [4] The Silver-Promoted Phosphonation/Alkynylation of Alkene Proceeding with Radical 1,2-Alkynyl Migration
    Jin, Shengnan
    Sung, Song
    Yu, Jin-Tao
    Cheng, Jiang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17): : 11177 - 11185
  • [5] Silver-catalyzed tandem heterocyclization/alkynylation of 1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles
    Mothe, Srinivasa Reddy
    Kothandaraman, Prasath
    Chan, Philip Wai Hong
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [6] Synthesis of Highly Substituted 3-Formylfurans by a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization Cascade
    Wang, Tao
    Shi, Shuai
    Hansmann, Max M.
    Rettenmeier, Eva
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (14) : 3715 - 3719
  • [7] Silver Triflate Catalyzed Tandem Heterocyclization/Alkynylation of 1-((2-Tosylamino)aryl)but-2-yne-1,4-diols to 2-Alkynyl Indoles
    Mothe, Srinivasa Reddy
    Kothandaraman, Prasath
    Lauw, Sherman Jun Liang
    Chin, Samuel Ming Wei
    Chan, Philip Wai Hong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) : 6133 - 6137
  • [8] Merging "Anti-Baldwin" 3-Exo-Dig Cyclization with 1,2-Alkynyl Migration for Radical Alkylalkynylation of Unactivated Olefins
    Zhao, Qi
    Ji, Xiao-Shuang
    Gao, Yi-Yun
    Hao, Wen-Juan
    Zhang, Ke-Ying
    Tu, Shu-Jiang
    Jiang, Bo
    [J]. ORGANIC LETTERS, 2018, 20 (12) : 3596 - 3600
  • [9] Gold-Catalyzed Oxidative Cyclization Involving Nucleophilic Attack to the Keto Group of α,α′-Dioxo Gold Carbene and 1,2-Alkynyl Migration: Synthesis of Furan-3-carboxylates
    Wang, Ali
    Lu, Mingduo
    Liu, Yuanhong
    [J]. ORGANIC LETTERS, 2021, 23 (17) : 6813 - 6818
  • [10] Synthesis of Highly Substituted N-(Furan-3-ylmethylene)benzenesulfonamides by a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization Cascade
    Wang, Tao
    Huang, Long
    Shi, Shuai
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (45) : 14868 - 14871