Protecting-group-free synthesis of carboxylic group substituted alkynes by Sonogashira coupling in water

被引:3
|
作者
Zhu, Xin-Yi [1 ]
Wang, Yang [1 ]
Bai, Fang [1 ]
Gao, Guo-Wei [1 ]
Men, Jian [1 ]
机构
[1] Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China
关键词
Halogenated aromatic acids; Sonogashira coupling; phenylacetylene; water; palladium acetate; ARYL BROMIDES; CATALYZED HETEROCYCLIZATION; EFFICIENT; COMPLEX; HALIDES; LIGAND; SUZUKI;
D O I
10.3998/ark.5550190.0012.a08
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective, economic and green synthesis of carboxylic group substituted alkynes by Sonogashira coupling of halogenated aromatic acids with phenylacetylene has been developed. The coupling reaction proceeds well using Pd(OAc)(2)/TPPTS-CuI as catalyst with K2CO3 as base in water. It is worth noting that this procedure avoids the protection/deprotection steps of carboxylic group and obtains the title compounds in good to excellent yields.
引用
收藏
页码:99 / +
页数:29
相关论文
共 50 条
  • [31] Synthesis of α-Substituted Alkenylammonium Salts through Suzuki-Miyaura and Sonogashira Coupling
    Yoshita, Aoi
    Sakakibara, Yota
    Murakami, Kei
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2023, 96 (03) : 303 - 305
  • [32] Copper-Free Sonogashira Coupling in Water with Linear Polystyrene-Stabilized PdO Nanoparticles
    Teratani, Takuto
    Ohtaka, Atsushi
    Kawashima, Takahiro
    Shimomura, Osamu
    Nomura, Ryoki
    SYNLETT, 2010, (15) : 2271 - 2274
  • [33] An efficient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling of 1-chloroisoquinolines in the formation of 1-alkynyl-3-substituted isoquinolines
    Prabakaran, K.
    Khan, F. Nawaz
    Jin, Jong Sung
    TETRAHEDRON LETTERS, 2011, 52 (20) : 2566 - 2570
  • [34] Base-Promoted Glycosylation Allows Protecting Group-Free and Stereoselective O-Glycosylation of Carboxylic Acids
    Zuo, Hao
    Zhang, Chen
    Zhang, Yang
    Niu, Dawen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (42)
  • [35] HMPA-Free Synthesis of TMS-Substituted Alkynes
    Cordier, Marie
    Mueller, Daniel S.
    Devillard, Marc
    ORGANOMETALLICS, 2024, 43 (09) : 929 - 933
  • [36] Pd-catalyzed atom-efficient cross-coupling of triarylbismuth reagents with protecting group-free iodophenylmethanols: Synthesis of biarylmethanols
    Rao, Maddali L. N.
    Meka, Suresh
    TETRAHEDRON LETTERS, 2020, 61 (13)
  • [37] Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of β-urea glycosides in aqueous solution
    Ichikawa, Yoshiyasu
    Minami, Takahiro
    Kusaba, Shohei
    Saeki, Nobuyoshi
    Tonegawa, Yuta
    Tomita, Yumiko
    Nakano, Keiji
    Kotsuki, Hiyoshizo
    Masuda, Toshiya
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (23) : 3924 - 3931
  • [38] Synthesis of new 2-substituted pyrazolo[5,1-b][1,3]oxazoles via Sonogashira coupling reactions in water
    Bakherad, Mohammad
    Doosti, Rahele
    Mirzaee, Mahdi
    Jadidi, Khosro
    TETRAHEDRON, 2017, 73 (23) : 3281 - 3287
  • [39] Iron-Catalyzed Sonogashira Type Cross-Coupling Reaction of Aryl Iodides with Terminal Alkynes in Water under Aerobic Conditions
    Sindhu, Kallikkakam S.
    Thankachan, Amrutha P.
    Thomas, Anns Maria
    Anilkumar, Gopinathan
    CHEMISTRYSELECT, 2016, 1 (03): : 556 - 559
  • [40] Copper-free Sonogashira coupling reactions catalyzed by a water-soluble Pd-salen complex under aerobic conditions
    Bakherad, Mohammad
    Keivanloo, Ali
    Bahramian, Bahram
    Hashemi, Mahdieh
    TETRAHEDRON LETTERS, 2009, 50 (14) : 1557 - 1559