72758-73-7Relevant academic research and scientific papers
Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes
Yatabe, Takafumi,Mizuno, Noritaka,Yamaguchi, Kazuya
, p. 11564 - 11569 (2018)
Although hydroacylation is a very useful reaction for producing ketones from aldehydes with 100% atom efficiency, classical Rh-catalyzed hydroacylation presents several problems, including the need for transition metal catalysts, unwanted decarbonylation of aldehydes, and difficulty in regioselectivity control. However, formal hydroacylation utilizing the nucleophilicity of terminal alkynes can avoid these problems. In this work, we have achieved transition-metal-free formal hydroacylation of terminal alkynes using an Mg3Al-CO3-layered double hydroxide as a heterogeneous catalyst. This system was applicable to the efficient synthesis of α,β-unsaturated ketones with various substituents, and the catalyst can be reused without a significant loss of catalytic performance.
Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects
Hall, Thomas H.,Adams, Hannah,Vyas, Vijyesh K.,Michael Chu,Wills, Martin
, (2020/12/07)
A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.
Carbon-carbon bond formation in acid deep eutectic solvent: Chalcones synthesis: Via Claisen-Schmidt reaction
Tiecco, Matteo,Germani, Raimondo,Cardellini, Fabio
, p. 43740 - 43747 (2016/05/24)
One of the most studied properties of novel organic solvents is represented by their use as media for many chemical reactions. In this field Ionic Liquids (ILs) and more recently Deep Eutectic Solvents (DESs) have been playing significant roles for their smart properties. DESs are increasing their relevance thanks to their low toxicity, and because of their simple and cheap preparation that can be carried out by simply mixing two compounds. In this work we present the studies of the use of an acid DES obtained from 3-(cyclohexyldimethylammonio)propane-1-sulfonate and (1S)-(+)-10-camphorsulfonic acid (SB3-Cy/CSA) as reaction media and catalyst for carbon-carbon bond formation reaction via Claisen-Schmidt condensation. This powerful and widely used aldol condensation was performed without the use of any catalysts that are usually needed in this reaction, because of the presence of acid CSA in the DES components. We synthesised fourteen substituted chalcones from benzaldehydes and substituted benzaldehydes in combination with acetophenone and substituted acetophenones as probe reactions. The advantages of the use of this DES in this relevant reaction are represented by: the green properties of the media and its low toxicity; the absence of harmful acids to catalyse the aldol condensation because of the camphorsulfonic acid composing the DES mixture; the recycling and the re-use of the DES in subsequent reaction cycles; the mild conditions and the excellent conversions and yields observed.
Fly-ash:H2SO4 catalyzed solvent free efficient synthesis of some aryl chalcones under microwave irradiation
Thirunarayanan,Mayavel,Thirumurthy
experimental part, p. 18 - 22 (2012/05/05)
Some 2E aryl chalcones have been synthesized using greener catalyst Fly-ash:H2SO4 assisted solvent free environmentally benign Crossed-Aldol reaction. The yields of chalcones are more than 90%. The synthesized chalcones are characterized by their physical constants and spectral data.
Development of a general palladium-catalyzed carbonylative heck reaction of aryl halides
Wu, Xiao-Feng,Neumann, Helfried,Spannenberg, Anke,Schulz, Thomas,Jiao, Haijun,Beller, Matthias
supporting information; experimental part, p. 14596 - 14602 (2010/12/24)
The first general palladium-catalyzed carbonylative vinylation of aryl halides with olefins in the presence of CO has been developed. Applying a catalyst system consisting of [(cinnamyl)PdCl]2 and bulky imidazolyl-phosphine ligand L1 allows for the efficient and selective synthesis of α,β-unsaturated ketones under mild reaction conditions. Starting from easily available aryl halides and olefins, versatile building blocks can be prepared in a straightforward manner. The generality and functional group tolerance of this novel protocol is demonstrated.
Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base
Ishikawa, Teruhiko,Mizuta, Tomohiro,Hagiwara, Kumiko,Aikawa, Toshiaki,Kudo, Takayuki,Saito, Seiki
, p. 3702 - 3705 (2007/10/03)
Catalytic alkynylation of diverse ketones and aldehydes using nonmetallic benzyltrimethylammonium hydroxide or a basic resin of the hydroxide type in DMSO is described. Aliphatic or alicyclic carbonyl partners gave satisfactory results, whereas aromatic o
Synthesis and Characterization of Fluorescent 4,6-Disubstituted-3-cyano-2-methylpyridines
Matsui, Masaki,Oji, Akira,Hiramatsu, Koichi,Shibata, Katsuyoshi,Muramatsu, Hiroshige
, p. 201 - 206 (2007/10/02)
4,6-Disubstituted-3-cyano-2-methylpyridines, easily prepared by treating α,b-unsaturated carbonyl compounds with β-aminocrotononitrile in the presence of potassium tert-butoxide, have been found to show intense fluorescence in the region of 400-552 nm. 3-
