Highly Efficient Alkene Epoxidation and Aziridination Catalyzed by Iron(II) Salt + 4,4′,4′′-Trichloro-2,2′:6′,2′′-terpyridine/4,4′′-Dichloro-4′-<i>O</i>-PEG-OCH₃-2,2′:6′,2′′-terpyridine

“Iron(II) salt + 4,4′,4′′-trichloro-2,2′:6′,2′′-terpyridine” is an effective catalyst for epoxidation and aziridination of alkenes and intramolecular amidation of sulfamate esters. The epoxidation of allylic-substituted cycloalkenes achieved excellent diastereoselectivities up to 90%. ESI−MS results supported the formation of iron−oxo and −imido intermediates. Derivitization of Cl3terpy to O-PEG-OCH3−Cl2terpy renders the terpyridine unit to be recyclable, and the “iron(II) salt + 4,4′′-dichloro-4′-O-PEG-OCH3-2,2′:6′,2′′-terpyridine” protocol can be reused without a significant loss of catalytic activity in the alkene epoxidation.