Iron complex catalyzed selective C-H bond oxidation with broad substrate scope

TitleIron complex catalyzed selective C-H bond oxidation with broad substrate scope
Publication TypeJournal Article
Year of Publication2017
AuthorsJana, S, Ghosh, M, Ambule, M, Gupta, SSen
JournalOrganic Letters
Volume19
Issue4
Pagination746-749
Date PublishedFEB
Abstract

The use of a peroxidase-mimicking Fe complex has been reported on the basis of the biuret-modified TAML macrocyclic ligand 'framework (Fe-bTAML) as a catalyst to perform selective oxidation of unactivated 3 degrees C-H bonds and activated 2 degrees C-H bonds with low catalyst loading (1 mol %) and high product yield (excellent mass balance) under near neutral conditions and broad substrate scope (18 substrates which includes arenes, heteroaromatics, and polar functional groups). Aliphatic C-H oxidation of 3 and 2 sites of complex substrates was achieved with predictable selectivity using steric, electronic, and stereoelectronic rules that govern site selectivity, which included oxidation of (+)-artemisinin to (+)-10 beta-hydroxyartemisinin. Mechanistic studies indicate Fe-V(O) to be the active oxidant during these reactions.

DOI10.1021/acs.orglett.6b03359
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.732

Divison category: 
Chemical Engineering & Process Development

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