Glycerol - A on-innocent solvent for Rh-catalysed Pauson-Khand carbocyclisations

F. Chahdoura (1) , L. Dubrulle , Kévin Fourmy (2) , Jérôme J. Durand (2) , D. Madec (1) , M. Gomez (1)

1 LHFA - Laboratoire Hétérochimie Fondamentale et Appliquée
2 LCC - Laboratoire de chimie de coordination

Rh-catalysed carbocyclisations of the 1,6-enynes 1-8 efficiently gave bicyclo[3.3.0]octenones in neat glycerol. Unexpectedly, ligand-free [Rh(μ-OMe)(cod)]2 was highly selective. Moreover, TPPTS [tris(3-sulfonatophenyl)phosphane trisodium salt] improved the catalyst performance at low Rh/L ratios, but surprisingly, ligand excess blocked the reaction. Detailed NMR studies evidenced the role of glycerol in the catalytic process.

Mots clés: C-C coupling; Rhodium; Reaction mechanisms; NMR spectroscopy; Glycerol

Domaines: Chimie

F. Chahdoura, L. Dubrulle, Kévin Fourmy, Jérôme J. Durand, D. Madec, et al.. Glycerol - A on-innocent solvent for Rh-catalysed Pauson-Khand carbocyclisations. European Journal of Inorganic Chemistry, 2013, 2013 (29), pp.5138-5144. ⟨10.1002/ejic.201300651⟩. ⟨hal-00993534⟩