Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates

Filipa Siopa (1, 2) , Valérie-Anne Ramis Cladera (1) , Carlos Alberto Mateus Afonso (2) , Julie Oble (3, 4) , Giovanni Poli (3)

1 IPCM - Institut Parisien de Chimie Moléculaire
2 ULISBOA - Universidade de Lisboa = University of Lisbon
3 ROCS - Réactivité organométallique et catalyse pour la synthèse
4 CASCH - CAtalysis and Sustainable CHemistry

A Ru(0)-catalyzed direct C-H arylation and alkenylation of furfural imines with aryl-or alkenyl-boronates, in the presence of benzylideneacetone as a sacrificial hydride acceptor, is disclosed. This reaction provides access, after hydrolysis, to C3-arylated or vinylated furfural derivatives, and thus valorizes these relevant building-blocks obtained from lignocellulosic biomass. This approach, involving C-H activation by a Ru(0)/Ru(II), cycle offers several advantages, notably simple, mild and neutral reaction conditions.

Domaines: Chimie organique; Catalyse

Filipa Siopa, Valérie-Anne Ramis Cladera, Carlos Alberto Mateus Afonso, Julie Oble, Giovanni Poli. Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates. European Journal of Organic Chemistry, 2018, 2018 (44), pp.6101-6106. ⟨10.1002/ejoc.201800767⟩. ⟨hal-01975395⟩