25739-23-5Relevant articles and documents
Microwave-assisted copper catalyzed coupling reaction of aryl halides with terminal alkynes
Wang, Jin-Xian,Liu, Zhanxiang,Hu, Yulai,Wei, Bangguo,Kang, Liqin
, p. 1937 - 1945 (2002)
Coupling reaction of aryl halides with terminal alkynes using catalyst system of copper (I)-triphenylphosphine proceeds efficiently in the presence of potassium carbonate under microwave irradiation to give the corresponding unsymmetrical acetylenes in go
Hybrid hydrogels loaded with palladium nanoparticles – Catalysts for environmentally-friendly Sonogashira and Heck cross-coupling reactions
Slavik, Petr,Smith, David K.
, (2020/07/07)
Palladium nanoparticles (PdNPs) were encapsulated within hybrid hydrogels made from an acylhydrazide-functionalised 1,3:2,4-dibenzylidene sorbitol (DBS-CONHNH2) low-molecular-weight gelator (LMWG) combined with agarose polymer gelator via in situ reduction of Pd(II). These heterogeneous gel-phase catalysts were successfully applied for copper-, amine- and phosphine-free Sonogashira cross-coupling reactions under environmentally-friendly conditions without the need for inert atmosphere reaction conditions. The PdNP-loaded gel was reused in Sonogashira couplings up to at least five times with no adverse effect on yield. The performance of solvated PdNP-loaded gel catalysts was compared with the dried xerogels. The xerogels can be used at higher temperatures, enhancing reaction kinetics albeit lowering reaction selectivity, but unlike the solvated gels, were unable to be easily recycled and reused. The PdNP-loaded gels also had good activity in Heck reactions, and although longer reaction times or higher temperatures were required than for the Sonogashira reaction, the reaction conditions were mild for a Heck coupling. In summary, we demonstrate a ‘waste-to-wealth’ methodology in which Pd(II) ‘waste’ is converted into a valuable gel-phase catalyst that can be used for green Sonogashira and Heck cross-coupling reactions.
The CuFe2O4@SiO2@ZrO2/SO42-/Cu nanoparticles: An efficient magnetically recyclable multifunctional Lewis/Br?nsted acid nanocatalyst for the ligand- and Pd-free Sonogashira cross-coupling reaction in water
Nasseri, Mohammad Ali,Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Allahresani, Ali
, p. 20749 - 20759 (2019/07/12)
Herein, the synthesis and application of copper-incorporated sulfated zirconium oxide supported on CuFe2O4 NPs (CuFe2O4@SiO2@ZrO2/SO42-/Cu NPs) as a novel Lewis/Br?nsted acid nanocatalyst were studied for the Sonogashira C-C cross-coupling reaction. The fabricated CuFe2O4@SiO2@ZrO2/SO42-/Cu catalyst exhibited efficient activity for a large variety of aryl iodides/bromides and, most importantly, aryl chlorides in water and in the presence of NaOH as a base in short reaction times. The catalyst was fully characterized by FTIR, TG-DTG, VSM, XRD, EDX, FE-SEM and TEM analyses. A synergetic effect could be considered to have arisen from the various Lewis acid and Br?nsted acid sites present in the catalyst. The efficient incorporation of copper into zirconia provided a robust highly stable hybrid, which prevented any metal leaching, whether from the magnetite moiety and/or Cu sites in the reaction mixture. Moreover, the catalyst was successfully recovered from the mixture by a simple external magnet and reused for at least 9 consecutive runs. Zero metal leaching, stability, consistency with a variety of substrates, fast performance, cost-effectiveness, environmental friendliness, and preparation with accessible and cheap materials are some of the advantages and highlights of the current protocol.
