Metal-free, Bronsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids

被引：27
|
作者：
Choi, Hyuck [1 ]
Kim, Jaehyun [1 ]
Lee, Kooyeon [1 ,2 ]
机构：
[1] Kangwon Natl Univ, Dept Biohlth Technol, Chunchon 200701, South Korea
[2] Kangwon Natl Univ, Inst Biosci & Biotechnol, Chunchon 200701, South Korea
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 32期
基金：
新加坡国家研究基金会;
关键词：
Coumarin; Bronsted acid; Trifluoromethanesulfonic acid; Condensation; Cyclization; N-SULFONYL AZIDES; C-H BONDS; HYDROAMINATIONS; COMPLEXES; CYCLIZATION; MILD;
D O I：
10.1016/j.tetlet.2016.06.039
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel synthesis of coumarin derivatives by Bronsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields. (C) 2016 Published by Elsevier Ltd.
引用
收藏
页码：3600 / 3603
页数：4
相关论文
共 50 条
  • [41] Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Aznar, Fernando
    Valdes, Carlos
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) : 4993 - 4996
  • [42] Transition Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives
    Zhu, Chen
    Falck, John R.
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2395 - 2410
  • [43] Stereocontrolled Cyanohydrin Ether Synthesis through Chiral Bronsted Acid-Mediated Vinyl Ether Hydrocyanation
    Lu, Chunliang
    Su, Xiaoge
    Floreancig, Paul E.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9366 - 9376
  • [44] Metal-Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes
    Seo, Eunkyeong
    Oh, Jonghoon
    Lee, Sunwoo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (11) : 1774 - 1777
  • [45] Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide
    Wu, Xiang-mei
    Lou, Jia-ming
    Yan, Guo-bing
    SYNLETT, 2016, 27 (15) : 2269 - 2273
  • [46] Bronsted acid-promoted thiazole synthesis under metal-free conditions using sulfur powder as the sulfur source
    Ni, Penghui
    Tan, Jing
    Li, Rong
    Huang, Huawen
    Zhang, Feng
    Deng, Guo-Jun
    RSC ADVANCES, 2020, 10 (07) : 3931 - 3935
  • [47] Diversity-Oriented Synthesis of Chromenes via Metal-Free Domino Reactions from Ketones and Phenols
    Xue, Wei-Jian
    Li, Qi
    Gao, Fang-fang
    Zhu, Yan-ping
    Wang, Jun-gang
    Zhang, Wei
    Wu, An-Xin
    ACS COMBINATORIAL SCIENCE, 2012, 14 (08) : 478 - 483
  • [48] Metal-Free Dehomologative Oxidation of Arylacetic Acids for the Synthesis of Aryl Carboxylic Acids
    Kalmode, Hanuman P.
    Vadagaonkar, Kamlesh S.
    Shinde, Suresh L.
    Chaskar, Atul C.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07): : 3781 - 3786
  • [49] Synthesis of Substituted Coumarins via Bronsted Acid Mediated Condensation of Allenes with Substituted Phenols or Anisoles
    Kim, Sundae
    Kang, Dongjin
    Lee, Chang-Hee
    Lee, Phil Ho
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15): : 6530 - 6537
  • [50] Liquid-crystalline coumarin derivatives: contribution to the tailoring of metal-free sensitizers for solar cells
    Merlo, Aloir A.
    Tavares, Aline
    Khan, Sherdil
    Leite Santos, Marcos J.
    Teixeira, Sergio Ribeiro
    LIQUID CRYSTALS, 2018, 45 (02) : 310 - 322
12345