Biologically inspired nonheme iron complex-catalyzed cis-dihydroxylation of alkenes modeling Rieske dioxygenases

Coordination Chemistry Reviews - Tập 477 - Trang 214945 - 2023
Jie Chen1, Wenxun Song1, Yong-Min Lee2, Wonwoo Nam2, Bin Wang1
1School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250022, China
2Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea

Tài liệu tham khảo

Noe, 2005, Asymmetric dihydroxylation of alkenes, 109 Kolb, 1994, Catalytic asymmetric dihydroxylation, Chem. Rev., 94, 2483, 10.1021/cr00032a009 Heravi, 2017, Applications of Sharpless asymmetric dihydroxylation in the total synthesis of natural products, Tetrahedron: Asymmetry, 28, 987, 10.1016/j.tetasy.2017.07.004 Gao, 1988, Vicinal diol cyclic sulfates. Like epoxides only more reactive, J. Am. Chem. Soc., 110, 7538, 10.1021/ja00230a045 Kim, 1989, Cyclic sulfates containing acid-sensitive groups and chemoselective hydrolysis of sulfate esters, Tetrahedron Lett., 30, 655, 10.1016/S0040-4039(01)80274-4 Fleming, 1991, Selective transformations of threo-2,3-dihydroxy esters, J. Org. Chem., 56, 2869, 10.1021/jo00008a051 Ko, 1995, Vicinal diol cyclic thionocarbonates: Similar to cyclic sulfates, but more reactive, J. Org. Chem., 60, 6250, 10.1021/jo00125a003 Ko, 2002, Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters: Synthesis of statine and its diastereomer, J. Org. Chem., 67, 2689, 10.1021/jo015967f Bhowmick, 2006, Syntheses and applications of C2-symmetric chiral diols, Tetrahedron: Asymmetry, 17, 1901, 10.1016/j.tetasy.2006.06.023 Sundermeier, 2004, Recent developments in the osmium-catalyzed dihydroxylation of olefins, 1 Martínez, 2018, Dioxygenation of alkenes, 309 Zaitsev, 2006, Recent developments in asymmetric dihydroxylations, Synthesis, 11, 1725 Bataille, 2011, Osmium-free direct syn-dihydroxylation of alkenes, Chem. Soc. Rev., 40, 114, 10.1039/B923880H Ottenbacher, 2019, Recent advances in catalytic asymmetric dihydroxylation of olefins, Russ. Chem. Rev., 88, 1094, 10.1070/RCR4904 Achard, 2021, Recent advances on catalytic osmium-free olefin syn-dihydroxylation, Eur. J. Org. Chem., 2021, 877, 10.1002/ejoc.202001209 Su, 2021, Catalytic asymmetric osmium-free dihydroxylation of alkenes, Synthesis, 53, 1229, 10.1055/a-1325-4092 Shing, 1994, Practical and rapid vicinal hydroxylation of alkenes by catalytic ruthenium tetraoxide, Angew. Chem. Int. Ed., 33, 2312, 10.1002/anie.199423121 Shing, 1996, Ruthenium-catalyzed cis-dihydroxylation of alkenes: Scope and limitations, Chem. Eur. J., 2, 50, 10.1002/chem.19960020111 Plietker, 2003, An improved protocol for the RuO4-catalyzed dihydroxylation of olefins, Org. Lett., 5, 3353, 10.1021/ol035335a Plietker, 2005, Selectivity versus reactivity - recent advances in RuO4-catalyzed oxidations, Synthesis, 15, 2453, 10.1055/s-2005-872172 Ho, 2004, Ruthenium nanoparticles supported on hydroxyapatite as an efficient and recyclable catalyst for cis-dihydroxylation and oxidative cleavage of alkenes, Angew. Chem. Int. Ed., 43, 3303, 10.1002/anie.200453703 Yip, 2005, Alkene cis-dihydroxylation by [(Me3tacn)(CF3CO2)RuVIO2]ClO4 (Me3tacn = 1,4,7-Trimethyl-1,4,7-triazacyclononane): Structural characterization of [3 + 2] cycloadducts and kinetic studies, J. Am. Chem. Soc., 127, 14239, 10.1021/ja0528230 Yip, 2008, Homogeneous [RuIII(Me3tacn)Cl3]-catalyzed alkene cis-dihydroxylation with aqueous hydrogen peroxide, Chem. Asian J., 3, 70, 10.1002/asia.200700237 Hentges, 1980, Asymmetric induction in the reaction of osmium tetroxide with olefins, J. Am. Chem. Soc., 102, 4263, 10.1021/ja00532a050 Jacobsen, 1988, Asymmetric dihydroxylation via ligand-accelerated catalysis, J. Am. Chem. Soc., 110, 1968, 10.1021/ja00214a053 Johnson, 2000, Asymmetric oxidations and related reactions: Catalytic asymmetric dihydroxylation–discovery and development, 357 Enthaler, 2011, Palladium-catalysed hydroxylation and alkoxylation, Chem. Soc. Rev., 40, 4912, 10.1039/c1cs15085e Tian, 2021, Palladium-catalysed enantioselective diacetoxylation of terminal alkenes, Nat. Catal., 4, 172, 10.1038/s41929-021-00574-5 Hao, 2016, Chiral-substituted poly-N-vinylpyrrolidinones and bimetallic nanoclusters in catalytic asymmetric oxidation reactions, J. Am. Chem. Soc., 138, 16839, 10.1021/jacs.6b12113 Eisink, 2021, Manganese-catalyzed dihydroxylation and epoxidation of olefins, 323 Kasper, 2021, Mechanisms in manganese oxidation catalysis with 1,4,7-triazacyclononane based ligands, 143, 10.1016/bs.adioch.2021.05.001 Saisaha, 2013, Mechanisms in manganese catalysed oxidation of alkenes with H2O2, Chem. Soc. Rev., 42, 2059, 10.1039/C2CS35443H De Vos, 1999, Selective alkene oxidation with H2O2 and a heterogenized Mn catalyst: Epoxidation and a new entry to vicinal cis-diols, Angew. Chem. Int. Ed., 38, 980, 10.1002/(SICI)1521-3773(19990401)38:7<980::AID-ANIE980>3.0.CO;2-W Brinksma, 2002, Homogeneous cis-dihydroxylation and epoxidation of olefins with high H2O2 efficiency by mixed manganese/activated carbonyl catalyst system, Tetrahedron Lett., 43, 2619, 10.1016/S0040-4039(02)00292-7 de Boer, 2005, cis-Dihydroxylation and epoxidation of alkenes by [Mn2O(RCO2)2(tmtacn)2]: Tailoring the selectivity of a highly H2O2-efficient catalyst, J. Am. Chem. Soc., 127, 7990, 10.1021/ja050990u de Boer, 2008, Manganese catalysed asymmetric cis-dihydroxylation with H2O2, Chem. Commun., 3747, 10.1039/b808355j Saisaha, 2010, Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2, Org. Biomol. Chem., 8, 4444, 10.1039/c0ob00102c Schoenfeldt, 2011, Manganese triazacyclononane oxidation catalysts grafted under reaction conditions on solid cocatalytic supports, J. Am. Chem. Soc., 133, 18684, 10.1021/ja204761e Chow, 2011, Practical manganese-catalysed highly enantioselective cis-dihydroxylation of electron-deficient alkenes and detection of a cis-dioxomanganese(V) intermediate by high resolution ESI-MS analysis, Chem. Commun., 47, 11204, 10.1039/c1cc11999k Brown, 2001, Asymmetric permanganate-promoted oxidative cyclization of 1,5-dienes by using chiral phase-transfer catalysis, Angew. Chem. Int. Ed., 40, 4496, 10.1002/1521-3773(20011203)40:23<4496::AID-ANIE4496>3.0.CO;2-F Bhunnoo, 2002, An asymmetric phase-transfer dihydroxylation reaction, Angew. Chem. Int. Ed., 41, 3479, 10.1002/1521-3773(20020916)41:18<3479::AID-ANIE3479>3.0.CO;2-O Wang, 2015, Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium, J. Am. Chem. Soc., 137, 10677, 10.1021/jacs.5b05792 Kovaleva, 2008, Versatility of biological non-heme Fe(II) centers in oxygen activation reactions, Nat. Chem. Biol., 4, 186, 10.1038/nchembio.71 Özgen, 2019, Rieske non-heme iron dioxygenases: Applications and future perspectives, 57 Guo, 2021, 8.14 - Non-heme mono-iron enzymes: Co-substrate-independent dioxygen activation, 301 Wang, 2017, Oxygen activation by mononuclear nonheme iron dioxygenases involved in the degradation of aromatics, J. Biol. Inorg. Chem., 22, 395, 10.1007/s00775-017-1436-5 Kal, 2017, Dioxygen activation by nonheme iron enzymes with the 2-His-1-carboxylate facial triad that generate high-valent oxoiron oxidants, J. Biol. Inorg. Chem., 22, 339, 10.1007/s00775-016-1431-2 Boyd, 2006, Arene cis-dihydrodiol formation: From biology to application, Org. Biomol. Chem., 4, 181, 10.1039/B513226F Barry, 2013, Mechanism and catalytic diversity of Rieske non-heme iron-dependent oxygenases, ACS Catal., 3, 2362, 10.1021/cs400087p Ferraro, 2005, Rieske business: Structure–function of Rieske non-heme oxygenases, Biochem. Biophys. Res. Commun., 338, 175, 10.1016/j.bbrc.2005.08.222 Bugg, 2008, Non-heme iron-dependent dioxygenases: Unravelling catalytic mechanisms for complex enzymatic oxidations, Curr. Opin. Chem. Biol., 12, 134, 10.1016/j.cbpa.2007.12.007 Karlsson, 2003, Crystal structure of naphthalene dioxygenase: Side-on binding of dioxygen to iron, Science, 299, 1039, 10.1126/science.1078020 Wolfe, 2003, Hydrogen peroxide-coupled cis-diol formation catalyzed by naphthalene 1,2-dioxygenase, J. Biol. Chem., 278, 829, 10.1074/jbc.M209604200 Neibergall, 2007, Hydrogen peroxide dependent cis-dihydroxylation of benzoate by fully oxidized benzoate 1,2-dioxygenase, Biochemistry, 46, 8004, 10.1021/bi700120j Chen, 2020, Artificial nonheme iron and manganese oxygenases for enantioselective olefin epoxidation and alkane hydroxylation reactions, Coord. Chem. Rev., 421, 213443, 10.1016/j.ccr.2020.213443 Vicens, 2018, Biomimetic oxidation in organic synthesis, 113 Company, 2011, Bioinspired non-heme iron catalysts in C-H and C=C oxidation reactions, 148 Oldenburg, 2008, Bio-inspired iron-catalyzed olefin oxidations: epoxidation versus cis-dihydroxylation, 451 Oldenburg, 2006, Bio-inspired nonheme iron catalysts for olefin oxidation, Catal. Today, 117, 15, 10.1016/j.cattod.2006.05.022 Bugg, 2003, Dioxygenase enzymes: Catalytic mechanisms and chemical models, Tetrahedron, 59, 7075, 10.1016/S0040-4020(03)00944-X Costas, 2004, Dioxygen activation at mononuclear nonheme iron active sites: Enzymes, models, and intermediates, Chem. Rev., 104, 939, 10.1021/cr020628n Que, 2008, Biologically inspired oxidation catalysis, Nature, 455, 333, 10.1038/nature07371 Bruijnincx, 2008, Mononuclear non-heme iron enzymes with the 2-His-1-carboxylate facial triad: Recent developments in enzymology and modeling studies, Chem. Soc. Rev., 37, 2716, 10.1039/b707179p Talsi, 2012, Chemo- and stereoselective C-H oxidations and epoxidations/cis-dihydroxylations with H2O2, catalyzed by non-heme iron and manganese complexes, Coord. Chem. Rev., 256, 1418, 10.1016/j.ccr.2012.04.005 Vicens, 2020, Rational design of bioinspired catalysts for selective oxidations, ACS Catal., 10, 8611, 10.1021/acscatal.0c02073 Olivo, 2017, Oxidation of alkane and alkene moieties with biologically inspired nonheme iron catalysts and hydrogen peroxide: From free radicals to stereoselective transformations, J. Biol. Inorg. Chem., 22, 425, 10.1007/s00775-016-1434-z Codola, 2014, Aminopyridine iron and manganese complexes as molecular catalysts for challenging oxidative transformations, Prog. Inorg. Chem., 59, 447 Chen, 1999, cis-Dihydroxylation of olefins by a non-heme iron catalyst: A functional model for Rieske dioxygenases, Angew. Chem. Int. Ed., 38, 2227, 10.1002/(SICI)1521-3773(19990802)38:15<2227::AID-ANIE2227>3.0.CO;2-B Chen, 2002, Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts: Two faces of an FeIII-OOH coin, J. Am. Chem. Soc., 124, 3026, 10.1021/ja0120025 Zang, 1997, Models for nonheme iron intermediates: Structural basis for tuning the spin states of Fe(TPA) complexes, J. Am. Chem. Soc., 119, 4197, 10.1021/ja9638521 Kim, 1997, Stereospecific alkane hydroxylation with H2O2 catalyzed by an iron(II)–tris(2-pyridylmethyl)amine complex, J. Am. Chem. Soc., 119, 5964, 10.1021/ja9642572 Feng, 2009, Bio-inspired arene cis-dihydroxylation by a non-haem iron catalyst modeling the action of naphthalene dioxygenase, Chem. Commun., 50 Costas, 2001, Modeling Rieske dioxygenases: The first example of iron-catalyzed asymmetric cis-dihydroxylation of olefins, J. Am. Chem. Soc., 123, 6722, 10.1021/ja015601k Iyer, 2014, A chameleon catalyst for nonheme iron-promoted olefin oxidation, Chem. Commun., 50, 13777, 10.1039/C4CC06164K Feng, 2011, Iron-catalyzed olefin epoxidation and cis-dihydroxylation by tetraalkylcyclam complexes: The importance of cis-labile sites, ACS Catal., 1, 1035, 10.1021/cs200292h Suzuki, 2008, Iron-catalyzed asymmetric olefin cis-dihydroxylation with 97% enantiomeric excess, Angew. Chem. Int. Ed., 47, 1887, 10.1002/anie.200705061 Klopstra, 2004, Non-heme iron complexes for stereoselective oxidation: Tuning of the selectivity in dihydroxylation using different solvents, Eur. J. Inorg. Chem., 2004, 846, 10.1002/ejic.200300667 Bautz, 2007, Biomimetic high-valent non-heme iron oxidants for the cis-dihydroxylation and epoxidation of olefins, Angew. Chem. Int. Ed., 46, 8067, 10.1002/anie.200701681 Costas, 2002, Ligand topology tuning of iron-catalyzed hydrocarbon oxidations, Angew. Chem. Int. Ed., 41, 2179, 10.1002/1521-3773(20020617)41:12<2179::AID-ANIE2179>3.0.CO;2-F Company, 2008, A novel platform for modeling oxidative catalysis in non-heme iron oxygenases with unprecedented efficiency, Chem. Eur. J., 14, 5727, 10.1002/chem.200800724 Garcia-Bosch, 2012, Iron-catalyzed C-H hydroxylation and olefin cis-dihydroxylation using a single-electron oxidant and water as the oxygen-atom source, Chem. Eur. J., 18, 13269, 10.1002/chem.201202147 Mas-Ballesté, 2006, Ligand topology effects on olefin oxidations by bio-inspired [FeII(N2Py2)] catalysts, Chem. Eur. J., 12, 7489, 10.1002/chem.200600453 Bukowski, 2006, Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine–iron(II)/H2O2 systems, Angew. Chem. Int. Ed., 45, 3446, 10.1002/anie.200504357 Oldenburg, 2005, Iron-catalyzed olefin cis-dihydroxylation using a bio-inspired N, N, O-ligand, J. Am. Chem. Soc., 127, 15672, 10.1021/ja054947i Oldenburg, 2010, Olefin cis-dihydroxylation with bio-inspired iron catalysts. Evidence for an FeII/FeIV catalytic cycle, J. Am. Chem. Soc., 132, 17713, 10.1021/ja1021014 Bruijnincx, 2008, Iron(II) complexes with bio-inspired N, N, O ligands as oxidation catalysts: Olefin epoxidation and cis-dihydroxylation, Chem. Eur. J., 14, 1228, 10.1002/chem.200700573 Moelands, 2013, Bioinspired nonheme iron complexes derived from an extended series of N, N, O-ligated BAIP ligands, Inorg. Chem., 52, 7394, 10.1021/ic400096e Oldenburg, 2006, A structural and functional model for dioxygenases with a 2-his-1-carboxylate triad, Angew. Chem. Int. Ed., 45, 7975, 10.1002/anie.200603486 Gosiewska, 2007, Mononuclear diastereopure non-heme Fe(II) complexes of pentadentate ligands with pyrrolidinyl moieties: Structural studies, and alkene and sulfide oxidation, Inorg. Chim. Acta, 360, 405, 10.1016/j.ica.2006.08.009 Dungan, 2012, L-Proline-derived ligands to mimic the ‘2-his-1-carboxylate’ triad of the non-haem iron oxidase active site, Tetrahedron, 68, 3231, 10.1016/j.tet.2012.02.031 Barry, 2008, cis-Dihydroxylation of alkenes by a non-heme iron enzyme mimic, Synlett, 14, 2172 Barry, 2012, Investigating the oxidation of alkenes by non-heme iron enzyme mimics, Org. Biomol. Chem., 10, 7372, 10.1039/c2ob25834j Ryu, 2002, High conversion of olefins to cis-diols by non-heme iron catalysts and H2O2, Chem. Commun., 1288, 10.1039/b203154j Prat, 2013, The mechanism of stereospecific C-H oxidation by Fe(Pytacn) complexes: Bioinspired non-heme iron catalysts containing cis-labile exchangeable sites, Chem. Eur. J., 19, 6724, 10.1002/chem.201300110 Company, 2009, Olefin-dependent discrimination between two nonheme HO–FeV=O tautomeric species in catalytic H2O2 epoxidations, Chem. Eur. J., 15, 3359, 10.1002/chem.200802597 Prat, 2013, Assessing the impact of electronic and steric tuning of the ligand in the spin state and catalytic oxidation ability of the FeII(Pytacn) family of complexes, Inorg. Chem., 52, 9229, 10.1021/ic4004033 Prat, 2013, Fe(PyTACN)-Catalyzed cis-dihydroxylation of olefins with hydrogen peroxide, Adv. Synth. Catal., 355, 947, 10.1002/adsc.201200938 Spannring, 2014, Fe(6-Me-PyTACN)-catalyzed, one-pot oxidative cleavage of methyl oleate and oleic acid into carboxylic acids with H2O2 and NaIO4, Catal. Sci. Technol., 4, 708, 10.1039/c3cy00851g Borrell, 2017, Mechanistically driven development of an iron catalyst for selective syn-dihydroxylation of alkenes with aqueous hydrogen peroxide, J. Am. Chem. Soc., 139, 12821, 10.1021/jacs.7b07909 Borrell, 2018, Greening oxidation catalysis: Iron catalyzed alkene syn-dihydroxylation with aqueous hydrogen peroxide in green solvents, ACS Sustainable Chem. Eng., 6, 8410, 10.1021/acssuschemeng.8b00542 Chow, 2010, cis-Dihydroxylation of alkenes with oxone catalyzed by iron complexes of a macrocyclic tetraaza ligand and reaction mechanism by ESI-MS spectrometry and DFT calculations, J. Am. Chem. Soc., 132, 13229, 10.1021/ja100967g Zang, 2016, Highly enantioselective iron-catalyzed cis-dihydroxylation of alkenes with hydrogen peroxide oxidant via an FeIII-OOH reactive intermediate, Angew. Chem. Int. Ed., 55, 10253, 10.1002/anie.201603410 Wei, 2020, Iron-catalyzed highly enantioselective cis-dihydroxylation of trisubstituted alkenes with aqueous H2O2, Angew. Chem. Int. Ed., 59, 16561, 10.1002/anie.202002866 Chen, 2022, Nonheme iron-catalyzed enantioselective cis-dihydroxylation of aliphatic acrylates as mimics of Rieske dioxygenases, CCS Chem., 4, 2369, 10.31635/ccschem.022.202201780 Fujita, 2003, Iron-catalyzed olefin cis-dihydroxylation by H2O2: Electrophilic versus nucleophilic mechanisms, J. Am. Chem. Soc., 125, 9912, 10.1021/ja029863d Kal, 2020, Bio-inspired nonheme iron oxidation catalysis: Involvement of oxoiron(V) oxidants in cleaving strong C-H bonds, Angew. Chem. Int. Ed., 59, 7332, 10.1002/anie.201906551 Hölzl, 2017, Speciation in iron epoxidation catalysis: A perspective on the discovery and role of non-heme iron(III)-hydroperoxo species in iron-catalyzed oxidation reactions, Coord. Chem. Rev., 352, 517, 10.1016/j.ccr.2017.09.015 Chen, 2002, Spin state tuning of non-heme iron-catalyzed hydrocarbon oxidations: Participation of FeIII–OOH and FeV=O intermediates, J. Chem. Soc., Dalton Trans, 672, 10.1039/b108629d Bassan, 2005, Two faces of a biomimetic non-heme HO-FeV=O oxidant: olefin epoxidation versus cis-dihydroxylation, Angew. Chem. Int. Ed., 44, 2939, 10.1002/anie.200463072 Bassan, 2005, A density functional study on a biomimetic non-heme iron catalyst: insights into alkane hydroxylation by a formally HO-FeV=O oxidant, Chem. Eur. J., 11, 692, 10.1002/chem.200400383 Quiñonero, 2005, Metal-peroxo versus metal-oxo oxidants in non-heme iron-catalyzed olefin oxidations: Computational and experimental studies on the effect of water, J. Am. Chem. Soc., 127, 6548, 10.1021/ja051062y Roy, 2018, Theoretical insights into the nature of oxidant and mechanism in the regioselective syn-dihydroxylation of an alkene with a Rieske oxygenase inspired iron catalyst, ChemCatChem, 10, 3683, 10.1002/cctc.201800799 Prat, 2011, Observation of Fe(V)=O using variable temperature mass spectrometry and its enzyme-like C-H and C=C oxidation reactions, Nat. Chem., 3, 788, 10.1038/nchem.1132 Xu, 2018, Detection of a transient FeV(O)(OH) species involved in olefin oxidation by a bio-inspired non-haem iron catalyst, Chem. Commun., 54, 8701, 10.1039/C8CC03990A Borrell, 2019, Characterized cis-FeV(O)(OH) intermediate mimics enzymatic oxidations in the gas phase, Nat. Commun., 10, 901, 10.1038/s41467-019-08668-2 Comba, 2007, A density functional theory study of the reaction of the biomimetic iron(II) complex of a tetradentate bispidine ligand with H2O2, Inorg. Chem., 46, 3826, 10.1021/ic061129y Bae, 2016, Mononuclear nonheme high-spin (S = 2) versus intermediate-spin (S = 1) iron(IV)-oxo complexes in oxidation reactions, Angew. Chem. Int. Ed., 55, 8027, 10.1002/anie.201603978 Kwon, 2015, Determination of spin inversion probability, H-tunneling correction, and regioselectivity in the two-state reactivity of nonheme iron(IV)-oxo complexes, J. Phys. Chem. Lett., 6, 1472, 10.1021/acs.jpclett.5b00527 Oloo, 2013, Cyclohexene as a substrate probe for the nature of the high-valent iron-oxo oxidant in Fe(TPA)-catalyzed oxidations, New J. Chem., 37, 3411, 10.1039/c3nj00524k Ghosh, 2021, 8.16 - Functional models for oxygen activating nonheme monoiron enzymes, 378 Paria, 2011, Oxidative decarboxylation of benzilic acid by a biomimetic iron(II) complex: Evidence for an iron(IV)-oxo-hydroxo oxidant from O2, Angew. Chem. Int. Ed., 50, 11129, 10.1002/anie.201103971 Paria, 2014, Reactivity of an iron-oxygen oxidant generated upon oxidative decarboxylation of biomimetic iron(II) α-hydroxy acid complexes, Inorg. Chem., 53, 2810, 10.1021/ic402443r Chatterjee, 2015, Olefin cis-dihydroxylation and aliphatic C-H bond oxygenation by a dioxygen-derived electrophilic iron-oxygen oxidant, Angew. Chem. Int. Ed., 54, 9338, 10.1002/anie.201502229 Chakraborty, 2017, Reductive activation of O2 by non-heme iron(II) benzilate complexes of N4 ligands: Effect of ligand topology on the reactivity of O2-derived oxidant, Inorg. Chem., 56, 359, 10.1021/acs.inorgchem.6b02282 Chatterjee, 2018, Bioinspired olefin cis-dihydroxylation and aliphatic C-H bond hydroxylation with dioxygen catalyzed by a nonheme iron complex, Inorg. Chem., 57, 10160, 10.1021/acs.inorgchem.8b01353