13141-38-3Relevant articles and documents
Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina
Kabalka, George W.,Wang, Lei,Namboodiri, Vasudevan,Pagni, Richard M.
, p. 5151 - 5154 (2000)
A microwave-enhanced, solventless Sonogashira coupling reaction has been developed. Terminal alkynes couple with aryl or alkenyl iodide on palladium- doped alumina in the presence of triphenylphosphine and cuprous iodide to provide high yields of products. (C) 2000 Published by Elsevier Science Ltd.
Effect of solvent polarity on N-H insertion versus rearrangement of alkylidene carbenes
Taber, Douglass F.,Plepys, Raymond A.
, p. 6045 - 6047 (2005)
Alkylidene carbenes, when generated from o-aminobenzophenones and lithiated trimethylsilyldiazomethane, give a mixture of alkyne (by rearrangement) and indole (by N-H insertion). It has been found that this ratio of indole to acetylene shows a linear dependence on the polarity of the ethereal solvent.
Magnetic Cu–Schiff base complex with an ionic tail as a recyclable bifunctional catalyst for base/Pd-free Sonogashira coupling reaction
Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali
, p. 2693 - 2705 (2019)
Abstract: A Cu(II)–Schiff base complex containing imidazolium ionic phase was prepared and decorated on γ-Fe2O3 magnetic nanoparticles (γ-Fe2O3@Cu(II)IL-SB) and found to be an efficient catalyst for the Pd- and base-free Sonogashira coupling reaction. The heterogeneous catalyst was characterized by FTIR spectroscopy, UV–visible spectroscopy, FE-SEM, TEM, XRD spectroscopy, EDX spectroscopy, VSM, ICP spectroscopy, and atomic absorption spectroscopy. The coupling reactions were performed using the catalyst under mild and base-free conditions, and high-to-excellent yields were obtained for a variety of substrates. The catalyst demonstrates a dual-functionality arising from metal sites and imidazolium moieties and that the later plays a base role. Reusability and stability of γ-Fe2O3@Cu(II)IL-SB were studied several times, which can be reused up to eight consecutive runs with at least reduction in catalytic activity. Also, the mechanism of this bifunctional catalytic system was thoroughly investigated. Graphic abstract: A new and efficient method has been developed for the base- and Pd-free Sonogashira cross-coupling reactions of aryl halides with phenyl acetylene using a bifunctional γ-Fe2O3@Cu(II)IL-SB catalyst with imidazolium moiety under mild conditions[Figure not available: see fulltext.].
Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
supporting information, p. 5599 - 5604 (2021/08/01)
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
, p. 10645 - 10660 (2020/09/18)
A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
