133886-40-5Relevant articles and documents
One-pot approach to access 2H-pyran-2-ones bearing an amino group via the Pd-catalyzed Sonogashira coupling of (Z)-3-iodovinylic esters followed by intramolecular iodocyclization
Mayooufi, Atef,Romdhani-Younes, Moufida,Jacquemin, Johan,Thibonnet, Jér?me
, (2019)
A one‐pot sequence of Sonogashira coupling and iodocyclization afforded novel amino-containing trisubstituted 2H-pyran-2-ones in good yields. This transformation proceeds via 1) synthesis of an ynenoic ester intermediate by a Sonogashira coupling reaction with an N-substituted (Z)-3-iodovinylic ester; 2) intramolecular iodocyclization of the latter intermediate under mildly basic conditions. The flexibility of this strategy enables the efficient syntheses of a variety of substituted 2H-pyran-2-ones.
Intermolecular transition metal-catalyzed [4 + 2 + 2] cycloaddition reactions: A new approach to the construction of eight-membered rings
Evans, P. Andrew,Robinson, John E.,Baum, Erich W.,Fazal, Aleem N.
, p. 8782 - 8783 (2002)
Transition metal-catalyzed cycloaddition reactions represent powerful methods for the construction of complex polycyclic systems. We have developed a new intermolecular metal-catalyzed [4 + 2 + 2] cycloaddition of heteroatom-tethered enyne derivatives wit
A Free Radical Cyclization Catalyzed by Ruthenium Hydride Species
Kim, Rira,Kwon, Kuktae,Lee, Hee-Yoon
supporting information, p. 3909 - 3913 (2021/10/23)
A photolytically generated ruthenium hydride species catalyzing a free radical cyclization reaction was developed. As the new methodology ensures reproducibility of the free radical reaction of trialkyltin hydrides and a fast hydrogen transfer to the radical intermediates, the methodology provides fast quenching of radical intermediates and thus suppresses rearrangement of radical intermediates before the hydride quench. By offering new reactivity and selectivity to the trialkyltin hydride mediated free radical cyclization reactions, the methodology will find wide range of applications in organic synthesis.
Gold(I) Complexes Nuclearity in Constrained Ferrocenyl Diphosphines: Dramatic Effect in Gold-Catalyzed Enyne Cycloisomerization
Nguyen, Tuan-Anh,Roger, Julien,Nasrallah, Houssein,Rampazzi, Vincent,Fournier, Sophie,Cattey, Hélène,Sosa Carrizo, E. Daiann,Fleurat-Lessard, Paul,Devillers, Charles H.,Pirio, Nadine,Lucas, Dominique,Hierso, Jean-Cyrille
, p. 2879 - 2885 (2020/08/13)
Di-tert-butylated-bis(phosphino)ferrocene ligands bearing phosphino substituents R (R=phenyl, cyclohexyl, iso-propyl, mesityl, or furyl) allow tuning the selective formation of Au(I) halide complexes. Thus, dinuclear linear two-coordinate, but also rare mononuclear trigonal three-coordinate and tetrahedral four-coordinate complexes were formed upon tuning of the conditions. Both Au(I) chloride and rarer Au(I) iodide complexes were synthesized, and their X-ray diffraction analysis are reported. The significance of the control of structure and nuclearity in Au(I) complexes is further illustrated herein by its strong effect on the efficiency and selectivity of gold-catalysed cycloisomerization. Cationic linear digold(I) bis(dicyclohexylphosphino) ferrocenes outperform other catalysts in the demanding regioselective cycloisomerization of enyne sulphonamides into cyclohexadienes. Conversely, tetrahedral and trigonal cationic monogold(I) complexes were found incompetent for enyne cycloaddition. We used the two-coordinate linear electron-rich Au(I) complex 2 b (R=Cy) to extend the scope of selective intramolecular cycloaddition of different 1,6-enyne sulfonylamines with high activity and excellent selectivity to the endo cyclohexadiene products.
Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups
Blieck, Rémi,Perego, Luca Alessandro,Ciofini, Ilaria,Grimaud, Laurence,Taillefer, Marc,Monnier, Florian
supporting information, p. 1225 - 1234 (2019/02/26)
A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.
