Formation of a peri -Bridged Phosphonio-Naphthalene by Cu-Mediated Phosphine-Aryl Coupling

Charlie Blons (1) , Maryne Duval (1) , Damien Delcroix (2) , Hélène Olivier-Bourbigou (2) , Sonia Mallet-Ladeira (3) , E. Daiann Sosa Carrizo (4) , Karinne Miqueu (4) , Abderrahmane Amgoune (1) , Didier Bourissou (1)

1 LHFA - Laboratoire Hétérochimie Fondamentale et Appliquée
2 IFPEN - IFP Energies nouvelles
3 ICT - Institut de Chimie de Toulouse
4 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

The peri-iodo naphthyl phosphine 1 reacts with CuI to give the peri-bridged phosphonio-naphthalene 2, which has been fully characterized (multi-nuclear NMR, MS, XRD). The outcome of the reaction differs markedly from that observed with gold. A two-step pathway involving P-assisted C-I oxidative addition to copper, followed by P-C reductive elimination is shown to be energetically feasible by DFT calculations.

Mots clés: naphthalene; phosphorus; P−C coupling; strained ring; copper

Domaines: Chimie théorique et/ou physique; Chimie analytique; Polymères; Matériaux

Charlie Blons, Maryne Duval, Damien Delcroix, Hélène Olivier-Bourbigou, Sonia Mallet-Ladeira, et al.. Formation of a peri -Bridged Phosphonio-Naphthalene by Cu-Mediated Phosphine-Aryl Coupling. Chemistry - A European Journal, 2018, 24 (46), pp.11922-11925. ⟨10.1002/chem.201802579⟩. ⟨hal-01836433⟩