Arranging both oxygen atoms of O2 for difunctionalized oxygenation

March 11, 2024

• Title:       

  Arranging both oxygen atoms of O2 for difunctionalized oxygenation

• Image Source:

  All at once arrangement of both oxygen atoms of dioxygen into aliphatic C(sp3)-C(sp3) bonds for hydroxyketone difunctionalization

• Mark:

  Scheme 1

• Associated context:

  Contrary to this very successful achievement in the industrial practice, the catalytic placement of both oxygen atoms of dioxygen within one hydrocarbon molecule for preparations of difunctionalized oxygenation fine chemicals is very rare. Until 2010,  Jiao and co-workers reported that both oxygen atoms of dioxygen could be transformed into an α-ketoamide unit via a  Cu-catalyzed oxidative amidation-deionization reaction of terminal alkynes (Scheme 1), although the substrates require certain functional groups (–NH2, –≡, and C=O) and the process results in partial hydrogen or oxygen atom loss from the substrates. However, few strategies on inserting both oxygen atoms of dioxygen into two genuine σ-C(sp3) positions within one organic molecule in a one-pot reaction have been reported so far.