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

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Abstract

"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 Cl 3terpy to O-PEG-OCH 3-Cl 2terpy renders the terpyridine unit to be recyclable, and the "iron(II) salt + 4,4''-dichloro-4'- O-PEG-OCH 3-2,2':6',2''-terpyridine" protocol can be reused without a significant loss of catalytic activity in the alkene epoxidation.

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