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Selective photocatalytic hydroxylation and epoxidation reactions by an iron complex using water as the oxygen source.


ABSTRACT: The iron complex [(bTAML)FeIII-OH2]- (1) selectively catalyses the photocatalytic hydroxylation and epoxidation reactions of alkanes and alkenes, respectively, using water as the oxygen-atom source. Upon the oxidation of unactivated alkanes, which included several substrates including natural products, hydroxylation was observed mostly at the 3° C-H bonds with 3°?:?2° selectivity up to ?100?:?1. When alkenes were used as the substrates, epoxides were predominantly formed with high yields. In the presence of H218O, more than 90% of the 18O-labelled oxygen atoms were incorporated into the hydroxylated and epoxide product indicating that water was the primary oxygen source. Mechanistic studies indicate the formation of an active [{(bTAML)FeIV}2-?-oxo]2- (2) dimer from the starting complex 1via PCET. The subsequent disproportionation of 2 upon addition of substrate, leading to the formation of FeV(O), renders the high selectivity observed in these reactions.

SUBMITTER: Chandra B 

PROVIDER: S-EPMC5676249 | biostudies-other | 2017 Nov

REPOSITORIES: biostudies-other

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Selective photocatalytic hydroxylation and epoxidation reactions by an iron complex using water as the oxygen source.

Chandra Bittu B   Singh Kundan K KK   Gupta Sayam Sen SS  

Chemical science 20170904 11


The iron complex [(bTAML)Fe<sup>III</sup>-OH<sub>2</sub>]<sup>-</sup> (<b>1</b>) selectively catalyses the photocatalytic hydroxylation and epoxidation reactions of alkanes and alkenes, respectively, using water as the oxygen-atom source. Upon the oxidation of unactivated alkanes, which included several substrates including natural products, hydroxylation was observed mostly at the 3° C-H bonds with 3° : 2° selectivity up to ∼100 : 1. When alkenes were used as the substrates, epoxides were predo  ...[more]

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