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Synthesis of Multisubstituted Allenes via Palladium-Catalyzed Cross-Coupling Reaction of Propargyl Acetates with an Organoaluminum Reagent

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We describe a convenient method for the synthesis of multisubstituted allenes from cross-coupling of propargyl acetates with ­organoaluminum reagent: The reaction of propargyl acetates with 1.2 equivalents of organoaluminum reagent mediated… Click to show full abstract

We describe a convenient method for the synthesis of multisubstituted allenes from cross-coupling of propargyl acetates with ­organoaluminum reagent: The reaction of propargyl acetates with 1.2 equivalents of organoaluminum reagent mediated by Pd(PPh 3 ) 2 Cl 2 (1 mol%)/Ph 3 P (2 mol%) and K 2 CO 3 in THF may produce tri- or tetrasubstituted allenes in good to excellent yields (83–94%) and high regio­selectivities (up to 99%) at 60 °C in 3–4 hours.

Keywords: organoaluminum reagent; multisubstituted allenes; synthesis multisubstituted; propargyl acetates; cross coupling

Journal Title: Synlett
Year Published: 2017

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