Generation Of Singlet Oxygen (O-1(2)) From Hydrogen Peroxide Decomposition By In Situ Generated Hypervalent Iodoarene Reagents

A novel method for the production of singlet oxygen from H2O2 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 (O-1(2)) under biphasic conditions. The existence of O-1(2) was demonstrated by trapping experiments with aromatic dienes, 1,3-cyclodienes, and alkenes. The mechanism of O-1(2) production from the iodoarene/MTO/35 % H2O2 system and the reaction scope was also discussed.