Aerobic alcohol oxidation and oxygen atom transfer reactions catalyzed by a nonheme iron(ii)-α-keto acid complex

Chemical Science
Debobrata Sheet, Tapan Kanti Paine

Abstract

α-Ketoglutarate-dependent enzymes catalyze many important biological oxidation/oxygenation reactions. Iron(iv)-oxo intermediates have been established as key oxidants in these oxidation reactions. While most reported model iron(ii)-α-keto acid complexes exhibit stoichiometric reactivity, selective oxidation of substrates with dioxygen catalyzed by biomimetic iron(ii)-α-keto acid complexes remains unexplored. In this direction, we have investigated the ability of an iron(ii) complex [(TpPh,Me)FeII(BF)] (1) (TpPh,Me = hydrotris(3-phenyl-5-methylpyrazolyl)borate and BF = monoanionic benzoylformate) to catalyze the aerobic oxidation of organic substrates. An iron-oxo oxidant, intercepted in the reaction of 1 with O2, selectively oxidizes sulfides to sulfoxides, alkenes to epoxides, and alcohols to the corresponding carbonyl compounds. The oxidant from 1 is able to hydroxylate the benzylic carbon of phenylacetic acid to afford mandelic acid with the incorporation of one oxygen atom from O2 into the product. The iron(ii)-benzoylformate complex oxidatively converts phenoxyacetic acids to the corresponding phenols, thereby mimicking the function of iron(ii)-α-ketoglutarate-dependent 2,4-dichlorophenoxyacetate dioxygenase (TfdA). Furthe...Continue Reading

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Citations

Jul 28, 2018·Angewandte Chemie·Hans SterckxBert U W Maes
May 18, 2017·Chemical Communications : Chem Comm·Kundan K Singh, Sayam Sen Gupta
Jan 27, 2017·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Giorgio OlivoMiquel Costas
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Dec 17, 2020·Chemistry : a European Journal·Emily C MonkcomRobertus J M Klein Gebbink
Apr 29, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Sandip MunshiTapan Kanti Paine
May 13, 2021·Inorganic Chemistry·Donghyun Jeong, Jaeheung Cho
Mar 17, 2018·Journal of the American Chemical Society·Hai-Jun ZhangLiang Yin

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Methods Mentioned

BETA
X-ray
infrared spectroscopy
NMR

Software Mentioned

SQUEEZE
APEX

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