40888-21-9Relevant academic research and scientific papers
Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.
supporting information, p. 558 - 564 (2020/12/07)
Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).
Palladium(II)-Catalyzed Direct Access to Indeno[1,2-c]isochromen-5(11H)-Ones via Intramolecular Oxypalladation-Initiated Cascade Process
Karuppasamy, Muthu,Vachan,Jandial, Tanvi,Babiola Annes, Sesuraj,Bhuvanesh, Nattamai,Uma Maheswari,Sridharan, Vellaisamy
supporting information, p. 2716 - 2724 (2020/06/01)
A palladium(II)-catalyzed cascade approach was established for the synthesis of indeno[1,2-c]isochromen-5(11H)-ones starting from 2-alkynyl tert-butyl benzoates bearing a pendant α,β-unsaturated carbonyl moiety in high yields (up to 99%) under mild condit
Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones
Faggyas, Réka J.,Grace, Megan,Williams, Lewis,Sutherland, Andrew
, p. 12595 - 12608 (2018/10/15)
A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck-Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines as substrates, the one-pot tandem process was extended for the direct synthesis of 3,4-dihydroquinolin-2-ones. In this case, following diazotization and Heck-Matsuda coupling to give methyl cinnamates, addition of hydrogen and reutilization of the palladium catalyst for reduction of the nitro group and hydrogenation of the alkene resulted in efficient formation of 3,4-dihydroquinolin-2-ones. The synthetic utility of this one-pot, four-stage process was demonstrated with the five-pot synthesis of a quinolinone-based sodium ion channel modulator.
Synthesis of carbo- and heterocycles via palladium catalysed cascade allene insertion-nucleophile incorporation-Michael addition processes
Grigg, Ronald,Inman, Martyn,Kilner, Colin,K?ppen, Ines,Marchbank, John,Selby, Peter,Sridharan, Visuvanathar
, p. 6152 - 6169 (2008/02/04)
Novel palladium catalysed two- and three-component thermal (conventional heating and microwave) cascade processes are described involving allenylation of an aryl iodide to generate a (π-allyl)palladium species, which are intercepted (inter- or intramolecularly) by a carbon or nitrogen nucleophile followed by intramolecular Michael addition to afford carbo- and heterocycles in good yields.
Synthesis of a Novel C2-Symmetric Thiourea and Its Application in the Pd-Catalyzed Cross-Coupling Reactions with Arenediazonium Salts under Aerobic Conditions
Dai, Mingji,Liang, Bo,Wang, Cuihua,Chen, Jiahua,Yang, Zhen
, p. 221 - 224 (2007/10/03)
(Matrix presented) A novel thiourea-based C2-symmetric ligand was synthesized, and its application in the palladium-catalyzed Heck and Suzuki coupling reactions of arenediazonium salts was evaluated. The reactions, which were performed at room temperature, without added base, and under aerobic conditions, produced product in 4 h with good yield. The corresponding arenediazonium salts were easily generated in one step from anilines.
Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations
Gibson, Susan E.,Guillo, Nathalie,Middleton, Richard J.,Thuilliez, Audrey,Tozer, Matthew J.
, p. 447 - 455 (2007/10/03)
The novel conformationally constrained phenylalanine analogues 2,3,4,5-tetrahydro-1H-3-benzazepine-2-carboxylic acid (Sic) 1, 1,2,3,4,5,6-hexahydro-3-benzazocine-2-carboxylic acid (Hic) 2 and 2,3,4,5,6,7-hexahydro-1H-3-benzazonine-2-carboxylic acid (Nic)
The synthesis of bridged-ring carbo- and hetero-cycles via palladium catalysed regiospecific cyclisation reactions
Grigg,Santhakumar,Sridharan,Stevenson,Teasdale,Thornton-Pett,Worakun
, p. 9703 - 9720 (2007/10/02)
A catalyst system comprising 10 mol % (Pd(OAc)) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in
