Chemistry Letters, Vol.48, No.11, 1402-1405, 2019
Palladium(0)-catalyzed [4+2] Annulation of Salicylaldehydes and Propargyl Carbonates to Produce 3,4-Dihydro-2-methylene-2H-1-benzopyran-4-ols
Palladium(0)-catalyzed synthesis of 3,4-dihydro-2-methyl-ene-2H-1-benzopyran-4-ols via annulation between salicylaldehyde and propargyl carbonate using a formate reductant is reported herein. The annulation proceeds via common addition of the hydroxyl group in salicylaldehyde to the central carbon of eta(3)-allenyl-/propargylpalladium, wherein the latter is generated through the oxidative addition of propargyl carbonate to the catalyst and subsequent intramolecular umpolung allylation of the aldehyde.