Palladium-catalyzed, ligand-free SN2’ substitution reactions of organoaluminum with propargyl acetates for the synthesis of multi-substituted allenes

We describe a convenient method for the synthesis of multi-substituted allenes from SN2′ substitution reactions organoaluminum with propargyl acetates: The SN2′ substitution reaction of organoaluminum (0.4 mmol) with propargyl acetates (0.5 mmol) mediated by PdCl2(dppf) (1 mol%) at 60 °C in THF without ligand could produce multi-substituted allenes in moderate to good yields (up to 98%) and high selectivities (up to 99%). Their structures have been determined by HRMS and 1H (13C)NMR data.Graphical abstract

Source: Journal of Organometallic Chemistry - July 5, 2018 Category: Chemistry Source Type: research