Nucleophilic substitution of propargyl alcohols with aliphatic alcohols, aliphatic amines and heterocycles catalyzed by 4-nitrobenzenesulfonic acid: a scalable and metal-free process

被引：15
|
作者：
Savarimuthu, S. Antony [1 ]
Prakash, D. G. Leo [2 ]
Thomas, S. Augustine [1 ]
机构：
[1] St Xaviers Coll, Dept Chem, Palayankottai 627002, Tamil Nadu, India
[2] Univ Swansea, Sch Engn, Mat Res Ctr, Swansea SA2 8PP, W Glam, Wales
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 21期
关键词：
Propargyl alcohol; Propargyl ether; Propargyl amine; Heterocycles; Sulfonic acids; FRIEDEL-CRAFTS ALKYLATION; C-O; INDOLES; ACTIVATION; ETHERS; DESIGN; CARBON;
D O I：
10.1016/j.tet1et.2014.02.086
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
It is aimed to provide a cost effective p-NBSA catalyzed nucleophilic substitution of propargyl alcohols with alcohols, amines and heterocycles, without employing corrosive and costly metal catalysts, toxic solvents and column chromatography for purification. A systematic study of C-C, C-N and C-O bond formation and efficacy of the scalability have also been confirmed. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3213 / 3217
页数：5
相关论文
共 31 条
  • [21] Metal-Free Oxidation of Alcohols to Their Corresponding Carbonyl Compounds Using NH4NO3/Silica Sulfuric Acid
    Zarei, Amin
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (07) : 2149 - 2155
  • [22] Phenolic 3° Phosphine Oxides as a Class of Metal-Free Catalysts for the Activation of C-O Bonds in Aliphatic Alcohols: Direct Synthesis of Catalyst Candidates, and Kinetic Studies
    Martin, Matthew A.
    Brown, Sadie L.
    Beres, Danielle R.
    Frederic, Wrebekah M.
    Banks, Ashley M.
    Bloomfield, Aaron J.
    INORGANICS, 2022, 10 (03)
  • [23] Metal-free n-Bu4NI-catalyzed direct synthesis of amides from alcohols and N,N-disubstituted formamides
    Li, Huamin
    Xie, Jin
    Xue, Qicai
    Cheng, Yixiang
    Zhu, Chengjian
    TETRAHEDRON LETTERS, 2012, 53 (48) : 6479 - 6482
  • [24] On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
    Payra, Soumen
    Saha, Arijit
    Banerjee, Subhash
    RSC ADVANCES, 2016, 6 (98) : 95951 - 95956
  • [25] Aliphatic alcohols oxidation with Hydrogen Peroxide in water catalyzed by supported Phosphotungstic acid (PTA) on Silica coated MgAl2O4 nanoparticles as a recoverable catalyst
    Hajavazzadeh, Reza
    Razi, Maryam Kargar
    Mahjoub, Ali Reza
    INTERNATIONAL JOURNAL OF NANO DIMENSION, 2019, 10 (01) : 69 - 77
  • [26] Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
    Zhuang, Hongfeng
    Lu, Nan
    Ji, Na
    Han, Feng
    Miao, Chengxia
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (24) : 5461 - 5472
  • [27] Metal-Free and Recyclable Route to Synthesize Polysubstituted Olefins via C-C Bond Construction from Direct Dehydrative Coupling of Alcohols or Alkenes with Alcohols Catalyzed by Sulfonic Acid-Functionalized Ionic Liquids
    Han, Feng
    Yang, Lei
    Li, Zhen
    Zhao, Yingwei
    Xia, Chungu
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2506 - 2516
  • [28] Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols:: Allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources
    Kimura, M
    Shimizu, M
    Shibata, K
    Tazoe, M
    Tamaru, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (29) : 3392 - 3395
  • [29] Alternative Functionalization of 2-(3,4-Dihalophenyl)-4H-chromen-4-ones via Metal-Free Nucleophilic Aromatic Fluorine Substitution and Palladium-Catalyzed Cross-Coupling Reactions
    Shcherbakov, Konstantin, V
    Panova, Mariya A.
    Burgart, Yanina, V
    Sinegubova, Ekaterina O.
    Orshanskaya, Iana R.
    Zarubaev, Vladimir V.
    Gerasimova, Natalia A.
    Evstigneeva, Natalia P.
    Saloutin, Victor, I
    CHEMISTRYSELECT, 2022, 7 (33):
  • [30] METAL-FREE SYNTHESIS OF N-CONTAINING HETEROCYCLES FROM o-SUBSTITUTED ANILINE DERIVATIVES VIA 2,4,6-TRIHYDROXYBENZOIC ACID-CATALYZED OXIDATIVE DEHYDROGENATION OF BENZYLAMINES UNDER OXYGEN ATMOSPHERE
    Kumazawa, Shun
    Uematsu, Akinori
    Dong, Chun-ping
    Kodama, Shintaro
    Nomoto, Akihiro
    Ueshima, Michio
    Ogawa, Akiya
    HETEROCYCLES, 2018, 97 (02) : 842 - 853
1234