Unusual propargylic oxidations catalyzed by chloroperoxidase.
This paper describes a new chloroperoxidase oxidative activity, namely, propargylic oxidations. Under appropriate conditions, chloroperoxidase catalyzes the oxidation of a variety of 2-alkynes to aldehydes via alcohol intermediates. Both hydrogen peroxide and t-butyl hydroperoxide can serve as terminal oxidants. The triple bond in the substrate is usually untouched. A free radical mechanism is proposed for the initial hydroxylation step in the overall reaction.
Hu
S
S
Department of Biochemistry, University of Illinois, Urbana 61801, USA.
Hager
L P
LP
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D002711:Chloride Peroxidase / Q000737:chemistry*; D003904:Mitosporic Fungi / Q000201:enzymology; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*
D000480:Alkynes; D020005:Propanols; C028255:propargyl alcohol; D002711:Chloride Peroxidase