Lithiation of prochiral 2,2'-dichloro-5,5'-dibromo-4,4'-bipyridine as a tool for the synthesis of chiral polyhalogenated 4,4'-bipyridines (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Lithiation of prochiral 2,2'-dichloro-5,5'-dibromo-4,4'-bipyridine as a tool for the synthesis of chiral polyhalogenated 4,4'-bipyridines (Articolo in rivista) (literal)

Anno

• 2013-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1021/jo401255q (literal)

Alternative label

• Mamane V., Aubert E., Peluso P., Cossu S. (2013)
  Lithiation of prochiral 2,2'-dichloro-5,5'-dibromo-4,4'-bipyridine as a tool for the synthesis of chiral polyhalogenated 4,4'-bipyridines
  in Journal of organic chemistry (Online)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Mamane V., Aubert E., Peluso P., Cossu S. (literal)

Pagina inizio

• 7683 (literal)

Pagina fine

• 7689 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

• http://pubs.acs.org/doi/abs/10.1021/jo401255q (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 78 (literal)

Rivista

• Journal of organic chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 7 (literal)

Note

• ISI Web of Science (WOS) (literal)
• Scopu (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• 1) Laboratoire SRSMC UMR CNRS 7565 Université de Lorraine, 54506 Vandoeuvre-les-Nancy, France; 2) Laboratoire CRM2 UMR CNRS 7036, Université de Lorraine, 54506 Vandoeuvre-les-Nancy, France; 3) Istituto di Chimica Biomolecolare, ICB-CNR, UOS di Sassari; 4) Università Ca' Foscari di Venezia, Dipartimento di Scienze Molecolari e Nanosistemi (literal)

Titolo

• Lithiation of prochiral 2,2'-dichloro-5,5'-dibromo-4,4'-bipyridine as a tool for the synthesis of chiral polyhalogenated 4,4'-bipyridines (literal)

Abstract

• Lithiation of the achiral tetrahalogenated 4,4'- bipyridine 1 with alkyllithiums was investigated. n-BuLi was found to induce either the chlorine-directed deprotolithiation reaction alone or with a concomitant halogen-lithium exchange furnishing after iodine trapping chiral 4,4'- bipyridines 2 and 6, respectively. The role of n-BuLi in the deprotolithiation process of 1 was elucidated on the basis of isolated secondary derivatives. After deprotolithiation, the lithiated species could be trapped by different electrophiles such as MeI, TMSCl, MeSSMe, R3SnCl (R = Me or n-Bu), and PPh2Cl. Moreover, 4,4'-bipyridine 2 was submitted to cross-coupling reactions (Suzuki and Sonogashira) which occurred selectively at the carbon-iodine bond. All compounds of this new family of atropisomeric 4,4'-bipyridines were separated by chiral HPLC (high-performance liquid chromatography), and the absolute configurations of obtained enantiomers were mainly assigned by XRD (X-ray diffraction) using anomalous dispersion. (literal)

Prodotto di

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Metodologie sintetiche a base multisettoriale per la costruzione di strutture molecolari complesse (PM.P01.011.005) (Modulo)

Autore CNR

• PAOLA PELUSO (Unità di personale interno)

Incoming links:

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Metodologie sintetiche a base multisettoriale per la costruzione di strutture molecolari complesse (PM.P01.011.005) (Modulo)

Autore CNR di

• PAOLA PELUSO (Unità di personale interno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Journal of organic chemistry (Rivista)