Ph-tetraMe-Bithienine, the First Member of the Class of Chiral Heterophosphepines: Synthesis, Electronic and Steric Properties, Metal Complexes and Catalytic Activity (Articolo in rivista)

Type
Label
  • Ph-tetraMe-Bithienine, the First Member of the Class of Chiral Heterophosphepines: Synthesis, Electronic and Steric Properties, Metal Complexes and Catalytic Activity (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/ejoc.201301098 (literal)
Alternative label
  • Vaghi Luca, Benincori Tiziana, Cirilli Roberto, Elisabetta Alberico, Mussini Romana Patrizia, Pierini Marco, Pilati Tullio, Rizzo Simona, Francesco Sannicolo (2013)
    Ph-tetraMe-Bithienine, the First Member of the Class of Chiral Heterophosphepines: Synthesis, Electronic and Steric Properties, Metal Complexes and Catalytic Activity
    in European journal of organic chemistry (Online)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Vaghi Luca, Benincori Tiziana, Cirilli Roberto, Elisabetta Alberico, Mussini Romana Patrizia, Pierini Marco, Pilati Tullio, Rizzo Simona, Francesco Sannicolo (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Vaghi Luca, Benincori Tiziana: Studi dell'Insubria, via Valleggio 11, 22100 Como, Italy Cirilli Roberto: Dipartimento del Farmaco, Istituto Superiore di Sanità, viale Regina Elena 299, 00161 Roma, Italy Mussini Romana Patrizia, Francesco Sannicolo: Dipartimento di Chimica and C.I.M.A.I.N.A., Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy Pierini Marco: Dipartimento di Chimica e Tecnologie del Farmaco, Università degli Studi di Roma \"La Sapienza\", Piazza Aldo Moro 5, 20100 Roma, Italy Pilati Tullio, Rizzo Simona: Istituto di Scienze e Tecnologie Molecolari, CNR, via Golgi 19, 20133 Milano, Italy (literal)
Titolo
  • Ph-tetraMe-Bithienine, the First Member of the Class of Chiral Heterophosphepines: Synthesis, Electronic and Steric Properties, Metal Complexes and Catalytic Activity (literal)
Abstract
  • Unknown 1H-2,7-dihydro-1-phenylphosphepine, containing a 2,2?,5,5?-tetramethyl-3,3?-bithiophene atropisomeric scaffold (Ph-tetraMe-Bithienine), and its oxide have been synthesized and structurally characterized by single-crystal Xray diffraction analysis. The most evident structural feature is the very small dihedral angle. The electronic properties of the phosphane were quantitatively evaluated by cyclic voltammetry and compared with three other 2,7-dihydro-1- phenylphosphepines differing in the nature of the biaromatic scaffold (biphenyl, 1,1?-binaphthyl and 2,2?-dimethoxybi-phenyl). The racemate of the phosphane oxide was resolved into antipodes, which were reduced to the enantiopure phosphanes and employed as ligands in Rh and Pt complexes in homogeneous stereoselective catalytic reactions. The enantioselective ability and catalytic activity of the new mediators were found to be quite modest in the hydrogenation reactions of olefinic double bonds, whereas good performances were achieved in specific C-C bond-forming reactions. The results are interpreted on the basis of the steric and electronic properties of the ligand. (literal)
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