54972-26-8Relevant academic research and scientific papers
CpTiCl2-Catalyzed Cross-Coupling between Internal Alkynes and Ketones: A Novel Concept in the Synthesis of Halogenated, Conjugated Dienes
Roldan-Molina, Esther,Nievas, Maria M.,Navarro, Jorge A. R.,Oltra, J. Enrique
supporting information, p. 8296 - 8301 (2020/06/17)
A novel concept for the synthesis of halogenated, conjugated dienes is disclosed: the CpTiCl2-catalyzed coupling of keto-alkynes, in the presence of Me3SiBr/Et3N?HBr. This reaction provided five-, six-, and seven-membered
Experimental and computational evidence on gold-catalyzed regioselective hydration of phthalimido-protected propargylamines: An entry to β-amino ketones
Arcadi, Antonio,Aschi, Massimiliano,Marsicano, Vincenzo,Michelet, Véronique
supporting information, p. 9438 - 9447 (2020/12/15)
The results of our investigations on the Au-catalyzed regioselective hydration reaction of both alkyl- A nd aryl-substituted N-propargyl phthalimides directed to the selective formation of the corresponding β-phthalimido ketones are described. Experimental data, in particular the observed regioselectivity, have been qualitatively supported by quantum-chemical calculations carried out on model systems in the framework of Density Functional Theory (DFT) followed by quantum theory of atoms in molecules (QTAIMS). Our results suggest that the electronic features of the initial adduct between the propargyl triple bond and the Au(i) catalyst, in particular the character of the gold-triple bond interaction, are essential for the observed regioselectivity. Other effects, such as the presence of the solvent and the formation of a H-bond between the water molecule and the phthalimido moiety, although apparently irrelevant for the regioselectivity, have proven to be kinetically and catalytically rather important. This journal is
Nucleophilic Isomerization of Epoxides by Pincer-Rhodium Catalysts: Activity Increase and Mechanistic Insights
Tian, Yingying,Jürgens, Eva,Mill, Katharina,Jordan, Ronja,Maulbetsch, Theo,Kunz, Doris
, p. 4028 - 4035 (2019/06/25)
Herein, we present the efficient isomerization of epoxides into methyl ketones with a novel pincer-rhodium complex under very mild conditions. The catalyst system has an excellent functional group tolerance and a wide array of epoxides was tested. The corresponding methyl ketones were obtained in very high yields with excellent chemo- and regioselectivity. In addition, we investigated mechanistic details like the isomerization of the catalyst, and we obtained evidence that the catalytic cycle follows a β-hydride elimination-reductive elimination pathway after the nucleophilic ring opening of the epoxide.
Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones
Tian, Yingying,Jürgens, Eva,Kunz, Doris
, p. 11340 - 11343 (2018/10/31)
The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.
Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes
Shibata, Nina,Tsuchiya, Takahisa,Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Ban, Shintaro,Tamura, Osamu
supporting information, p. 3025 - 3034 (2017/04/10)
ω-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclizat
Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature
Klumphu, Piyatida,Desfeux, Camille,Zhang, Yitao,Handa, Sachin,Gallou, Fabrice,Lipshutz, Bruce H.
, p. 6354 - 6358 (2017/08/29)
Several ppm level gold-catalyzed reactions enabled by the ligand HandaPhos can be performed at room temperature in aqueous nanoreactors composed of the surfactant Nok. Variously substituted allenes undergo cycloisomerization leading to heterocyclic products in good yields. Likewise, cyclodehydration is also illustrated under similar conditions, as is an intermolecular variant, hydration of terminal alkynes. Recycling of the catalyst and reaction medium is also illustrated. A low E factor associated with limited solvent use and therefore, waste generation, documents the greenness of this process.
Gold-Catalyzed Aminoalkenylation of β-Amino-1,n-Diynols to Cycloalkyl-, Piperidinyl- and Pyranyl-Fused Pyrroles
Kothandaraman, Prasath,Zhao, Yichao,Lee, Bo Ra,Le Ng, Clarrisa Jia,Lee, Jun Yi,Ayers, Benjamin James,Chan, Philip Wai Hong
, p. 1385 - 1391 (2016/05/19)
A synthetic method to prepare cycloalkyl-, piperidinyl- and pyranyl-fused pyrroles efficiently by gold(I)-catalyzed dehydrative aminoalkenylation of β-amino-1,n-diynols under mild conditions at room temperature is described.
Access to Polyfunctionalized Chiral Piperidines through Enantioselective Addition-Carbocyclization Cascade Reaction Catalyzed by a Rhodium(I)-Diene Complex
Serpier, Fabien,Brayer, Jean-Louis,Folléas, Beno?t,Darses, Sylvain
supporting information, p. 5496 - 5499 (2015/11/18)
A new addition-carbocyclization cascade reaction initiated by arylboronic acids and catalyzed by a rhodium/chiral diene complex is described. Starting from N-bridged oxoenoate derivatives, highly functionalized piperidines bearing three contiguous stereogenic centers were obtained with excellent enantio- and diastereoselectivities.
Preparation of cyclic β-amino acid derivatives with quaternary carbon center via a radical additioncyclization sequence
Takeda, Norihiko,Ueda, Masafumi,Kajisa, Seiko,Matsuno, Kenji,Naito, Takeaki,Miyata, Okiko
, p. 143 - 169 (2014/02/14)
A new method has been developed for the construction of α,α-disubstituted cyclic β-amino acid derivatives via the sulfanyl radical addition-cyclization reaction of oxime ether connected with acrylate. This reaction proceeded smoothly to give the cyclized products that contained a quaternary carbon center. Furthermore, the use of carbon centered radicals in the reaction allowed for the formation of cyclic amines containing various alkyl chains. The cyclized product with a quaternary carbon center could also be converted to sterically congested cyclic β-amino acid.
Ti-catalyzed straightforward synthesis of exocyclic allenes
Munoz-Bascon, Juan,Hernandez-Cervantes, Carmen,Padial, Natalia M.,Alvarez-Corral, Miriam,Rosales, Antonio,Rodriguez-Garcia, Ignacio,Oltra, J. Enrique
supporting information, p. 801 - 810 (2014/01/23)
Exocyclic allenes constitute useful building blocks in organic synthesis and have recently been identified as key intermediates in the synthesis of natural products. Here the first general method for the most straightforward synthesis of exocyclic allenes
