Pd-Promoted Cyclization of (Z)-Pent-2-en-4-yn-1-yl Alkanoates Leading to Furans via an Acyl Group Shift and Further Synthetic Transformation

Palladium-promoted acyl migration was observed in the reaction of (Z)-pent-2-en-4-yn-1-yl alkanoates in the presence of DBU to yield 2-(alkanoylmethyl)furan derivatives specialIntscript in high yields. Compounds 2 then underwent oxidative decarbonylation to afford 2-acylfurans with O2 as the oxidant under mild and metal-free conditions. The mechanistic pathway of the reaction involving an intramolecular cyclization and acyl group shift is discussed.

Automated summary

The study revealed that in the presence of Pd catalyst and DBU, (Z)-pent-2-en-4-yn-1-yl alkanoates can undergo acyl migration to yield high yields of 2-(alkanoylmethyl)furan derivatives, followed by oxidative decarbonylation with O2 to form 2-acylfurans. The mechanistic pathway involving intramolecular cyclization and acyl group shift was discussed.