Journal
NEW JOURNAL OF CHEMISTRY
Volume 37, Issue 11, Pages 3411-3415Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3nj00524k
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Funding
- US Department of Energy, Office of Basic Energy Sciences [DE-FG02-03ER15455]
- U.S. Department of Energy (DOE) [DE-FG02-03ER15455] Funding Source: U.S. Department of Energy (DOE)
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Cyclohexene is shown to be a versatile substrate probe in shedding light on the nature of the high-valent oxidant generated by bio-inspired nonheme iron catalysts. Cyclohexene provides the oxidant a choice to attack an allylic C-H bond or a CQC bond, and the selectivity observed should depend on the electronic properties of the oxidant. Allylic oxidation products are predominantly observed in the reaction with [Fe-IV(O)(TPA)(NCCH3)](2+) (TPA = tris(2-pyridylmethyl)amine), while epoxide and cis-diol are the major products found in the [Fe-II(TPA)(NCCH3)(2)](2+)-catalyzed reaction with H2O2. This difference suggests that the oxidant generated in the latter case must be distinct from [Fe-IV(O)(TPA)(NCCH3)](2+) and supports an oxoiron(V)-hydroxo species that has been proposed as the oxidant.
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