39833-49-3Relevant academic research and scientific papers
Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones
He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo
supporting information, p. 457 - 466 (2021/01/29)
An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is
Synthesis of Isoselenazoles and Isothiazoles from Demethoxylative Cycloaddition of Alkynyl Oxime Ethers
Zhang, Zhu-Zhu,Chen, Rong,Zhang, Xiao-Hong,Zhang, Xing-Guo
, p. 632 - 642 (2020/12/22)
A general method for the synthesis of isoselenazoles and isothiazoles has been developed by the base-promoted demethoxylative cycloaddition of alkynyl oxime ethers using the cheap and inactive Se powder and Na2S as selenium and sulfur sources. This transformation features the direct construction of N-, Se-, and S-containing heterocycles through the formation of N-Se/S and C-Se/S bonds in one-pot reactions with excellent functional group tolerance.
Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine
Cocoletzi-Xochitiotzi, Ana Patricia,Hernández-Hernández, Miguel,Medina-Mercado, Ignacio,Jiménez-Martínez, Williams De Jesús,Mastranzo, Virginia Maricela,Porcel, Susana
supporting information, p. 2379 - 2386 (2020/08/19)
Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z -isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.
Iron(III) chloride-promoted cyclization of α,-alkynic tosylhydrazones with diselenides: Synthesis of 4-(arylselanyl)-1: H-pyrazoles
Ji, Shun-Jun,Li, Fang-Hui,Li, Jian,Wang, Shun-Yi,Yao, Hai-Feng
supporting information, p. 1987 - 1993 (2020/03/23)
A highly efficient iron(iii) chloride-promoted cyclization between α,-alkynic tosylhydrazones and diselenides to form a 4-(arylselanyl)-1H-pyrazole skeleton is studied. This reaction forms C-N and C-Se bonds in one step by utilizing inexpensive iron(iii) chloride instead of expensive transition metal additives. This strategy features easily synthesized substrates, mild reaction conditions and high tolerance to functional groups.
Ionic liquid-mediated benzoyl transfer-coupling in the Suzuki and Sonogashira reactions and aryl transfer-coupling by decarbonylative Heck reaction, using N-Benzoyl-saccharin (NBSac) as reagent
Malunavar, Shruti S.,Sutar, Suraj M.,Prabhala, Pavankumar,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
, (2020/05/18)
The efficacy of N-benzoyl-saccharin (NBSac) as reagent for selective benzoyl transfer-coupling in the Suzuki reaction in BMIM-IL/[PAIM][NTf2] as solvent/base, and in the Sonogashira reaction employing guanidinium-IL (GIL) as solvent, are demonstrated. Decarbonylative aryl transfer-coupling occurs in the Heck reaction employing GIL as solvent. The reactions are catalyzed by Pd(OAc)2 or NiCl2(dppp), are performed under mild conditions in good yields, and have the potential for recycling/reuse of the IL solvent. Collectively, these methods provide facile access to diverse libraries of diarylketones, keto-ethynes and diaryl-ethenes.
Synthesis of 4,5-disubstituted-1H-1,2,3-triazoles
Rocha, Djenisa H. A.,Pinto, Diana C. G. A.,Silva, Artur M. S.
, p. 1479 - 1486 (2019/07/22)
Abstract: Two-step procedure, a palladium catalyzed Sonogashira cross-coupling reaction of aroyl chlorides with aryl acetylenes, and 1,3-dipolar cycloaddition of the 1,3-diarylprop-2-yn-1-ones with sodium azide under catalyst free conditions achieved the
Synthesis of (: Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid
Da Silva, Vitor A. F.,Da Silva, Gustavo P.,Matsuo, Bianca T.,Ali, Akbar,Davis, Rebecca L.,Zukerman-Schpector, Julio,Corrêa, Arlene G.,Paix?o, Márcio W.
supporting information, p. 519 - 526 (2019/01/24)
A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Br?nsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.
One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization
Thirukovela, Narasimha Swamy,Balaboina, Ramesh,Botla, Vinayak,Vadde, Ravinder,Jonnalagadda, Sreekantha Babu,Vasam, Chandra Sekhar
, p. 6471 - 6481 (2019/11/20)
Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.
TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-diaryl-1-CF3-indenes and versatility of the reaction mechanisms
Zerov, Aleksey V.,Kazakova, Anna N.,Boyarskaya, Irina A.,Panikorovskii, Taras L.,Suslonov, Vitalii V.,Khoroshilova, Olesya V.,Vasilyev, Aleksander V.
supporting information, (2018/11/30)
The TfOH-mediated reactions of 2,4-diaryl-1,1,1-trifluorobut-3-yn-2-oles (CF3-substituted diaryl propargyl alcohols) with arenes in CH2Cl2 afford 1,3-diaryl-1-CF3-indenes in yields up to 84%. This new process for synthesis of such CF3-indenes is complete
Method for preparing acetyenic ketone compound by using B-form DNA to promote Sonogashira reaction
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Paragraph 0014; 0028; 0029; 0030, (2018/09/08)
The invention discloses a method for preparing an acetyenic ketone compound by using B-form DNA to promote Sonogashira reaction. According to the method, the B-form DNA is used as an accelerant, purewater is used as a solvent, potassium carbonate is taken
