583872-73-5Relevant academic research and scientific papers
Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides
Mauleon, Pablo,Nunez, Angel A.,Alonso, Ines,Carretero, Juan C.
, p. 1511 - 1520 (2003)
Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of α,β-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)2 as catalyst, Ag2-CO3 as base in DMF at 120°C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene, The dominant formation of this 3:1 coupling product, instead of the Heck trisubstituted olefin, shows that aromatic C-H activation processes can compete with the usually fast syn β-hydrogen elimination step in the Heck arylation of an acyclic olefin. The structural scope of this palladium-catalyzed cascade arylation of α,β-unsaturated sulfones has proved to be wide with regard to substitution at the β-position (alkyl, aryl, or alkenyl substitution), substitution at the sulfone unit (alkyl or phenyl sulfones), and configuration at the C=C bond (trans or cis). Moreover, although less favored than in the case of the arylation of α,β-unsaturated sulfones, similarly substituted 9,10-dihydrophenanthrenes have also been obtained in the case of α,β-unsaturated phosphine oxides and α,β-unsaturated phosphonate esters. A Pd0-pdII-pdIV mechanistic pathway involving the successive formation of highly electrophilic σ-alkylpalladium intermediates and palladacycles is proposed for this multi-component arylation.
Direct sulfonylation of anilines mediated by visible light
Johnson, Tarn C.,Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,Maccoss, Malcolm,Dixon, Darren J.,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.
, p. 629 - 633 (2018/01/28)
Sulfones feature prominently in biologically active molecules and are key functional groups for organic synthesis. We report a mild, photoredox-catalyzed reaction for sulfonylation of aniline derivatives with sulfinate salts, and demonstrate the utility of the method by the late-stage functionalization of drugs. Key features of the method are the straightforward generation of sulfonyl radicals from bench-stable sulfinate salts and the use of simple aniline derivatives as convenient readily available coupling partners.
Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
Llamas, Tomas,Arrayas, Ramon Gomez,Carretero, Juan C.
, p. 1795 - 1798 (2007/10/03)
A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sulfones is described. Nearly complete exo selectivity and enantioselectivities up to 85% ee are attained with Cu(CH3CN)4
