Generation of singlet oxygen (1O2) from hydrogen peroxide decomposition by in situ generated hypervalent iodoarene reagents

Abstract

A novel method for the production of singlet oxygen from H 2O2 was developed. A combination of iodoarene (ArI), methyltrioxorhenium (MTO), and H2O2 in the presence of pyridine as the co-catalyst efficiently produced singlet molecular oxygen ( 1O2) under biphasic conditions. The existence of 1O2 was demonstrated by trapping experiments with aromatic dienes, 1,3-cyclodienes, and alkenes. The mechanism of 1O 2 production from the iodoarene/MTO/35 % H2O2 system and the reaction scope was also discussed. © 2014 IUPAC & De Gruyter Berlin/Boston 2014.