DBU-Mediated Oxidation of β-Dicarbonyls: Formation of Hydroxylated and Rearranged Products under Air Atmosphere

Abstract

AbstractThe oxidation of different β-dicarbonyls in acetonitrile has been explored under an air atmosphere in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The presence of DBU resulted in the formation of hydroxylated products or rearrangement products derived from hydroxylated products. Specifically, the transformation of 2-oxocyclopentanecarboxylates to 2-hydroxyhexanedioates was achieved with good yields when additional 1,2-bis(diphenylphosphino)ethane and ROH were present. DBU proved to be indispensable for this transformation and showed specificity beyond its usual role as a base.