Manganese(II) complexes of 1,1'-bis[(pyridin-2-yl)methyl)]-2,2'-bipiperidine (PYBP): Synthesis, structure, catalytic properties in alkene epoxidation with hydrogen peroxide, and related mechanistic studies

Yang, Guang; Mikhalyova, Elena A.; Filatov, Alexander S.; Kryatov, Sergiy V.; Rybak-Akimova, Elena V.

doi:10.1016/j.ica.2022.121288

Manganese(II) complexes of 1,1'-bis[(pyridin-2-yl)methyl)]-2,2'-bipiperidine (PYBP): Synthesis, structure, catalytic properties in alkene epoxidation with hydrogen peroxide, and related mechanistic studies

Journal Article · Tue Nov 15 00:00:00 EST 2022 · Inorganica Chimica Acta

DOI:https://doi.org/10.1016/j.ica.2022.121288· OSTI ID:2419158

Yang, Guang ^[1]; Mikhalyova, Elena A. ^[2]; Filatov, Alexander S. ^[3]; Kryatov, Sergiy V. ^[4]; Rybak-Akimova, Elena V. ^[4]

Tufts Univ., Medford, MA (United States); OSTI
National Academy of Sciences of Ukraine (NASU), Kiev (Ukraine)
Univ. of Chicago, IL (United States)
Tufts Univ., Medford, MA (United States)

In this study, several manganese(II) complexes with the stereoisomers of ligand PYBP (1,1'-bis[(pyridin-2-yl)methyl]-2,2'-bipiperidine) and different anions were prepared and characterized by X-ray diffractometry. Complex [Mn^II(rac-PYBP)]²⁺ (1) was found to be an efficient catalyst of alkene epoxidation by hydrogen peroxide in the presence of acetic acid in acetonitrile at room temperature. Cyclooctene was converted to its epoxide with up to 91 % yield, 99.6 % selectivity, and the turnover number of 180 within 5 min. Fast epoxidations of cyclohexene, 1-decene, styrene, and cis-stilbene were also achieved. Isomeric complex [Mn^II(meso-PYBP)]²⁺ (2) was catalytically inactive under the same experimental conditions. Stopped-flow spectrophotometry and freeze-quenched EPR spectra show that complex 2 is not oxidized by H₂O₂ in the presence of acetic acid (AcOH) but instead undergoes partial ligand protonation and liberation of the Mn²⁺ cations due to the relatively poor chelating ability of ligand meso-PYBP. The rac-PYBP isomer acts as a better ligand and retains the coordinated Mn center when complex 1 is treated with the H₂O₂/AcOH mixture in acetonitrile solution yielding a mixture of intensely colored intermediates likely involving Mn^III, Mn^IV, and Mn^V complexes. Magnetic susceptibility measurements, UV–vis and EPR spectra suggest that dinuclear complexes [Mn^III₂(μ-O)(μ-OAc)(rac-PYBP)₂]³⁺ and [Mn^IIIMn^IV(μ-O)₂(rac-PYBP)₂]³⁺ gradually accumulate in the reaction mixture as inactivated states of the catalyst. Complex 1 also causes fast decomposition of hydrogen peroxide into O₂ gas and H₂O, which competes with the epoxidation of alkenes and requires gradual addition of H₂O₂ for its efficient use. The catalytic activity of complex 1 is strongly influenced by its counterions and decreases in order ClO₄^- ≈ SbF₆^- > NO₃^– > Cl^- indicating that labile ligands in the coordination sphere of Mn are required for the activation of H₂O₂.

View Accepted Manuscript (DOE)

Research Organization:: Tufts Univ., Medford, MA (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: FG02-06ER15799

OSTI ID:: 2419158

Alternate ID(s):: OSTI ID: 1960870

Journal Information:: Inorganica Chimica Acta, Journal Name: Inorganica Chimica Acta Journal Issue: C Vol. 546; ISSN 0020-1693

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (82)

Reactivity and mechanisms of metalloporphyrin-catalyzed oxidations Groves, John T. Journal of Porphyrins and Phthalocyanines, Vol. 04, Issue 04 https://doi.org/10.1002/(SICI)1099-1409(200006/07)4:4<350::AID-JPP249>3.0.CO;2-G	journal	June 2000
In situ Formation of Peracetic Acid in Iron-Catalyzed Epoxidations by Hydrogen Peroxide in the Presence of Acetic Acid Fujita, Megumi; Que, Lawrence Advanced Synthesis & Catalysis, Vol. 346, Issue 23 https://doi.org/10.1002/adsc.200303204	journal	February 2004
A Broad Substrate-Scope Method for Fast, Efficient and Selective Hydrogen Peroxide-Epoxidation Garcia-Bosch, Isaac; Ribas, Xavi; Costas, Miquel Advanced Synthesis & Catalysis, Vol. 351, Issue 3 https://doi.org/10.1002/adsc.200800650	journal	February 2009
Non-Heme Manganese Complexes Catalyzed Asymmetric Epoxidation of Olefins by Peracetic Acid and Hydrogen Peroxide Ottenbacher, Roman V.; Bryliakov, Konstantin P.; Talsi, Evgenii P. Advanced Synthesis & Catalysis, Vol. 353, Issue 6 https://doi.org/10.1002/adsc.201100030	journal	April 2011
[Mn(tmc)(O2)]+: A Side-On Peroxido Manganese(III) Complex Bearing a Non-Heme Ligand Seo, Mi Sook; Kim, Ja Young; Annaraj, Jamespandi Angewandte Chemie International Edition, Vol. 46, Issue 3 https://doi.org/10.1002/anie.200603414	journal	January 2007
Iron-Catalyzed Asymmetric Olefincis-Dihydroxylation with 97 % Enantiomeric Excess Suzuki, Ken; Oldenburg, Paul D.; Que, Lawrence Angewandte Chemie International Edition, Vol. 47, Issue 10 https://doi.org/10.1002/anie.200705061	journal	February 2008
Structural Characterization and Remarkable Axial Ligand Effect on the Nucleophilic Reactivity of a Nonheme Manganese(III)-Peroxo Complex Annaraj, Jamespandi; Cho, Jaeheung; Lee, Yong-Min Angewandte Chemie International Edition, Vol. 48, Issue 23 https://doi.org/10.1002/anie.200900118	journal	May 2009
Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung Angewandte Chemie International Edition, Vol. 49, Issue 44 https://doi.org/10.1002/anie.201000819	journal	September 2010
Evidence for a Precursor Complex in CH Hydrogen Atom Transfer Reactions Mediated by a Manganese(IV) Oxo Complex Garcia-Bosch, Isaac; Company, Anna; Cady, Clyde W. Angewandte Chemie International Edition, Vol. 50, Issue 25 https://doi.org/10.1002/anie.201100907	journal	April 2011
Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid Jeong, Donghyun; Yan, James J.; Noh, Hyeonju Angewandte Chemie International Edition, Vol. 57, Issue 26 https://doi.org/10.1002/anie.201802641	journal	May 2018
Selectivity Trends in Olefin Epoxidations Catalyzed by (NNNN)Manganese(+II) Complexes using Trifluoroethanol as the Solvent Lorenz, Samuel; Plietker, Bernd ChemCatChem, Vol. 8, Issue 20 https://doi.org/10.1002/cctc.201600755	journal	September 2016
Conversion constants for redox potentials measured versus different reference electrodes in acetonitrile solutions at 25°C Pavlishchuk, Vitaly V.; Addison, Anthony W. Inorganica Chimica Acta, Vol. 298, Issue 1 https://doi.org/10.1016/S0020-1693(99)00407-7	journal	January 2000
Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes Irie, Ryo; Noda, Keiko; Ito, Yoshio Tetrahedron: Asymmetry, Vol. 2, Issue 7 https://doi.org/10.1016/S0957-4166(00)86102-9	journal	January 1991
Bioinspired Mn-aminopyridine catalyzed epoxidations of olefins with various oxidants: Enantioselectivity and mechanism Ottenbacher, Roman V.; Talsi, Evgenii P.; Bryliakov, Konstantin P. Catalysis Today, Vol. 278 https://doi.org/10.1016/j.cattod.2016.04.033	journal	December 2016
Active sites and mechanisms of bioinspired oxidation with H2O2, catalyzed by non-heme Fe and related Mn complexes Bryliakov, Konstantin P.; Talsi, Evgenii P. Coordination Chemistry Reviews, Vol. 276 https://doi.org/10.1016/j.ccr.2014.06.009	journal	September 2014
Artificial nonheme iron and manganese oxygenases for enantioselective olefin epoxidation and alkane hydroxylation reactions Chen, Jie; Jiang, Zhankun; Fukuzumi, Shunichi Coordination Chemistry Reviews, Vol. 421 https://doi.org/10.1016/j.ccr.2020.213443	journal	October 2020
Manganese(II) complexes of pyridyl-appended diazacyclo-alkanes: Effect of ligand backbone ring size on catalytic olefin oxidation Saravanan, Natarajan; Palaniandavar, Mallayan Inorganica Chimica Acta, Vol. 385 https://doi.org/10.1016/j.ica.2012.01.009	journal	April 2012
Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins Murphy, Andrew; Stack, T. Daniel P. Journal of Molecular Catalysis A: Chemical, Vol. 251, Issue 1-2 https://doi.org/10.1016/j.molcata.2006.01.042	journal	May 2006
Diiron(III) oxo-bridged complexes with BPMEN and additional monodentate or bidentate ligands: Synthesis and reactivity in olefin epoxidation with H2O2 Taktak, Sonia; Kryatov, Sergey V.; Haas, Terry E. Journal of Molecular Catalysis A: Chemical, Vol. 259, Issue 1-2 https://doi.org/10.1016/j.molcata.2006.05.071	journal	November 2006
Recent advances and perspectives in the manganese-catalysed epoxidation reactions Krishnan, K. Keerthi; Thomas, Anns Maria; Sindhu, Kallikkakam S. Tetrahedron, Vol. 72, Issue 1 https://doi.org/10.1016/j.tet.2015.11.003	journal	January 2016
Bioinspired Manganese and Iron Complexes for Enantioselective Oxidation Reactions: Ligand Design, Catalytic Activity, and Beyond Sun, Wei; Sun, Qiangsheng Accounts of Chemical Research, Vol. 52, Issue 8 https://doi.org/10.1021/acs.accounts.9b00285	journal	July 2019
Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H ₂ O ₂ and O ₂ Bryliakov, Konstantin P. Chemical Reviews, Vol. 117, Issue 17 https://doi.org/10.1021/acs.chemrev.7b00167	journal	August 2017
X-Band Electron Paramagnetic Resonance Comparison of Mononuclear Mn ^IV -oxo and Mn ^IV -hydroxo Complexes and Quantum Chemical Investigation of Mn ^IV Zero-Field Splitting Leto, Domenick F.; Massie, Allyssa A.; Colmer, Hannah E. Inorganic Chemistry, Vol. 55, Issue 7 https://doi.org/10.1021/acs.inorgchem.5b02309	journal	March 2016
Formation, Characterization, and O–O Bond Activation of a Peroxomanganese(III) Complex Supported by a Cross-Clamped Cyclam Ligand Colmer, Hannah E.; Howcroft, Anthony W.; Jackson, Timothy A. Inorganic Chemistry, Vol. 55, Issue 5 https://doi.org/10.1021/acs.inorgchem.5b02398	journal	February 2016
Kinetic Studies on the Oxoiron(IV) Complex with Tetradentate Aminopyridine Ligand PDP*: Restoration of Catalytic Activity by Reduction with H₂O₂ Piquette, Marc C.; Kryatov, Sergiy V.; Rybak-Akimova, Elena V. Inorganic Chemistry, Vol. 58, Issue 19 https://doi.org/10.1021/acs.inorgchem.9b02269	journal	September 2019
Enantioselective Epoxidations of Olefins with Various Oxidants on Bioinspired Mn Complexes: Evidence for Different Mechanisms and Chiral Additive Amplification Ottenbacher, Roman V.; Samsonenko, Denis G.; Talsi, Evgenii P. ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b02299	journal	January 2016
Mechanistic Insights into the Enantioselective Epoxidation of Olefins by Bioinspired Manganese Complexes: Role of Carboxylic Acid and Nature of Active Oxidant Du, Junyi; Miao, Chengxia; Xia, Chungu ACS Catalysis, Vol. 8, Issue 5 https://doi.org/10.1021/acscatal.8b00874	journal	April 2018
Metal-Catalyzed Epoxidations of Alkenes with Hydrogen Peroxide Lane, Benjamin S.; Burgess, Kevin Chemical Reviews, Vol. 103, Issue 7 https://doi.org/10.1021/cr020471z	journal	July 2003
Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation Xia, Q. -H.; Ge, H. -Q.; Ye, C. -P. Chemical Reviews, Vol. 105, Issue 5 https://doi.org/10.1021/cr0406458	journal	May 2005
Chiral Salen Complexes: An Overview to Recoverable and Reusable Homogeneous and Heterogeneous Catalysts Baleizão, Carlos; Garcia, Hermenegildo Chemical Reviews, Vol. 106, Issue 9 https://doi.org/10.1021/cr050973n	journal	September 2006
Asymmetric Epoxidations with H ₂ O ₂ on Fe and Mn Aminopyridine Catalysts: Probing the Nature of Active Species by Combined Electron Paramagnetic Resonance and Enantioselectivity Study Lyakin, Oleg Y.; Ottenbacher, Roman V.; Bryliakov, Konstantin P. ACS Catalysis, Vol. 2, Issue 6 https://doi.org/10.1021/cs300205n	journal	April 2012
Highly Enantioselective Bioinspired Epoxidation of Electron-Deficient Olefins with H ₂ O ₂ on Aminopyridine Mn Catalysts Ottenbacher, Roman V.; Samsonenko, Denis G.; Talsi, Evgenii P. ACS Catalysis, Vol. 4, Issue 5 https://doi.org/10.1021/cs500333c	journal	April 2014
Utilizing the Evans method with a superconducting NMR spectrometer in the undergraduate laboratory Schubert, Ernest M. Journal of Chemical Education, Vol. 69, Issue 1 https://doi.org/10.1021/ed069p62.1	journal	January 1992
Synthesis and Characterization of Complexes Containing the (.mu.-Oxo)(.mu.-acetato)dimanganese(III/III) Core Arulsamy, Navamoney; Glerup, Joergen; Hazell, Alan Inorganic Chemistry, Vol. 33, Issue 14 https://doi.org/10.1021/ic00092a001	journal	July 1994
Synthesis and Characterization of Bis(.mu.-oxo)dimanganese(III,III), -(III,IV), and -(IV,IV) Complexes with Ligands Related to N,N'-Bis(2-pyridylmethyl)-1,2-ethanediamine (Bispicen) Glerup, Jorgen; Goodson, Patricia A.; Hazell, Alan Inorganic Chemistry, Vol. 33, Issue 18 https://doi.org/10.1021/ic00096a040	journal	August 1994
Preparation of Highly Efficient Manganese Catalase Mimics ^‖ Triller, Michael U.; Hsieh, Wen-Yuan; Pecoraro, Vincent L. Inorganic Chemistry, Vol. 41, Issue 21 https://doi.org/10.1021/ic025897a	journal	October 2002
Synthesis, Structure, and Characterization of New Mononuclear Mn(II) Complexes. Electrochemical Conversion into New Oxo-Bridged Mn ₂ (III,IV) Complexes. Role of Chloride Ions Hureau, Christelle; Blondin, Geneviève; Charlot, Marie-France Inorganic Chemistry, Vol. 44, Issue 10 https://doi.org/10.1021/ic050243y	journal	May 2005
Reactivity of Mn^II with Superoxide. Evidence for a [Mn^IIIOO]⁺ Unit by Low-Temperature Spectroscopies Groni, Sihem; Blain, Guillaume; Guillot, Régis Inorganic Chemistry, Vol. 46, Issue 6 https://doi.org/10.1021/ic062063+	journal	February 2007
Synthesis and Catalytic Properties in Olefin Epoxidation of Novel Iron(II) Complexes with Pyridine-Containing Macrocycles Bearing an Aminopropyl Pendant Arm Taktak, Sonia; Ye, Wanhua; Herrera, Aida M. Inorganic Chemistry, Vol. 46, Issue 7 https://doi.org/10.1021/ic070094e	journal	April 2007
Oxo- and Hydroxomanganese(IV) Adducts: A Comparative Spectroscopic and Computational Study Chattopadhyay, Swarup; Geiger, Robert A.; Yin, Guochuan Inorganic Chemistry, Vol. 49, Issue 16 https://doi.org/10.1021/ic101014g	journal	August 2010
Nonheme Manganese-Catalyzed Asymmetric Oxidation. A Lewis Acid Activation versus Oxygen Rebound Mechanism: Evidence for the “Third Oxidant” Ottenbacher, Roman V.; Bryliakov, Konstantin P.; Talsi, Evgenii P. Inorganic Chemistry, Vol. 49, Issue 18 https://doi.org/10.1021/ic101297x	journal	September 2010
Lewis-Acid-Promoted Stoichiometric and Catalytic Oxidations by Manganese Complexes Having Cross-Bridged Cyclam Ligand: A Comprehensive Study Dong, Lei; Wang, Yujuan; Lv, Yanzong Inorganic Chemistry, Vol. 52, Issue 9 https://doi.org/10.1021/ic400361s	journal	April 2013
Influence of Calcium(II) and Chloride on the Oxidative Reactivity of a Manganese(II) Complex of a Cross-Bridged Cyclen Ligand Zhang, Zhan; Coats, Katherine L.; Chen, Zhuqi Inorganic Chemistry, Vol. 53, Issue 22 https://doi.org/10.1021/ic501342c	journal	October 2014
Mechanism of Cis-Dihydroxylation and Epoxidation of Alkenes by Highly H₂O₂ Efficient Dinuclear Manganese Catalysts de Boer, Johannes W.; Browne, Wesley R.; Brinksma, Jelle Inorganic Chemistry, Vol. 46, Issue 16 https://doi.org/10.1021/ic7003613	journal	July 2007
Reactivity of an Aminopyridine [LMn ^II ] ²⁺ Complex with H ₂ O ₂ . Detection of Intermediates at Low Temperature Groni, Sihem; Dorlet, Pierre; Blain, Guillaume Inorganic Chemistry, Vol. 47, Issue 8 https://doi.org/10.1021/ic702238z	journal	April 2008
Topologically Constrained Manganese(III) and Iron(III) Complexes of Two Cross-Bridged Tetraazamacrocycles Hubin, Timothy J.; McCormick, James M.; Alcock, Nathaniel W. Inorganic Chemistry, Vol. 40, Issue 3 https://doi.org/10.1021/ic9912225	journal	January 2001
Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane Jacobsen, Eric N.; Zhang, Wei; Muci, Alexander R. Journal of the American Chemical Society, Vol. 113, Issue 18 https://doi.org/10.1021/ja00018a068	journal	August 1991
Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes Zhang, Wei; Loebach, Jennifer L.; Wilson, Scott R. Journal of the American Chemical Society, Vol. 112, Issue 7 https://doi.org/10.1021/ja00163a052	journal	March 1990
Hydrocarbon oxidations with oxometalloporphinates. Isolation and reactions of a (porphinato)manganese(V) complex Groves, John T.; Kruper, William J.; Haushalter, Robert C. Journal of the American Chemical Society, Vol. 102, Issue 20 https://doi.org/10.1021/ja00540a050	journal	September 1980
A Synthetically Useful, Self-Assembling MMO Mimic System for Catalytic Alkene Epoxidation with Aqueous H ₂ O ₂ White, M. Christina; Doyle, Abigail G.; Jacobsen, Eric N. Journal of the American Chemical Society, Vol. 123, Issue 29 https://doi.org/10.1021/ja015884g	journal	July 2001
Efficient Epoxidation of Electron-Deficient Olefins with a Cationic Manganese Complex Murphy, Andrew; Dubois, Geraud; Stack, T. D. P. Journal of the American Chemical Society, Vol. 125, Issue 18 https://doi.org/10.1021/ja029962r	journal	May 2003
Olefin Oxygenation by the Hydroperoxide Adduct of a Nonheme Manganese(IV) Complex: Epoxidations by a Metallo−Peracid Produces Gentle Selective Oxidations Yin, Guochuan; Buchalova, Maria; Danby, Andrew M. Journal of the American Chemical Society, Vol. 127, Issue 49 https://doi.org/10.1021/ja055413k	journal	December 2005
Iron-Catalyzed Olefin Epoxidation in the Presence of Acetic Acid: Insights into the Nature of the Metal-Based Oxidant Mas-Ballesté, Rubén; Que, Lawrence Journal of the American Chemical Society, Vol. 129, Issue 51 https://doi.org/10.1021/ja075115i	journal	December 2007
Status of Reactive Non-Heme Metal–Oxygen Intermediates in Chemical and Enzymatic Reactions Ray, Kallol; Pfaff, Florian Felix; Wang, Bin Journal of the American Chemical Society, Vol. 136, Issue 40 https://doi.org/10.1021/ja507807v	journal	August 2014
New Iron(II) and Manganese(II) Complexes of Two Ultra-Rigid, Cross-Bridged Tetraazamacrocycles for Catalysis and Biomimicry Hubin, Timothy J.; McCormick, James M.; Collinson, Simon R. Journal of the American Chemical Society, Vol. 122, Issue 11 https://doi.org/10.1021/ja990366f	journal	March 2000
Structure and Reactivity of a Mononuclear Nonheme Manganese(III)–Iodosylarene Complex Jeong, Donghyun; Ohta, Takehiro; Cho, Jaeheung Journal of the American Chemical Society, Vol. 140, Issue 47 https://doi.org/10.1021/jacs.8b10244	journal	October 2018
Esters of 2-Iodoxybenzoic Acid: Hypervalent Iodine Oxidizing Reagents with a Pseudobenziodoxole Structure Zhdankin, Viktor V.; Koposov, Alexey Y.; Litvinov, Dmitry N. The Journal of Organic Chemistry, Vol. 70, Issue 16 https://doi.org/10.1021/jo051010r	journal	August 2005
The Conformations of Cyclooctene: Consequences for Epoxidation Chemistry Neuenschwander, Ulrich; Hermans, Ive The Journal of Organic Chemistry, Vol. 76, Issue 24 https://doi.org/10.1021/jo202176j	journal	November 2011
Biologically inspired oxidation catalysis Que, Lawrence; Tolman, William B. Nature, Vol. 455, Issue 7211 https://doi.org/10.1038/nature07371	journal	September 2008
Observation of Fe(V)=O using variable-temperature mass spectrometry and its enzyme-like C–H and C=C oxidation reactions Prat, Irene; Mathieson, Jennifer S.; Güell, Mireia Nature Chemistry, Vol. 3, Issue 10 https://doi.org/10.1038/nchem.1132	journal	September 2011
A new efficient ironcatalyst for olefinepoxidation with hydrogen peroxide Mikhalyova, Elena A.; Makhlynets, Olga V.; Palluccio, Taryn D. Chem. Commun., Vol. 48, Issue 5 https://doi.org/10.1039/C1CC15935F	journal	January 2012
Mechanisms in manganese catalysed oxidation of alkenes with H ₂ O ₂ Saisaha, Pattama; de Boer, Johannes W.; Browne, Wesley R. Chem. Soc. Rev., Vol. 42, Issue 5 https://doi.org/10.1039/C2CS35443H	journal	January 2013
Manganese complexes with non-porphyrin N₄ligands as recyclable catalyst for the asymmetric epoxidation of olefins Maity, Nabin Ch.; Kumar Bera, Prasanta; Ghosh, Debashis Catal. Sci. Technol., Vol. 4, Issue 1 https://doi.org/10.1039/C3CY00528C	journal	January 2014
Manganese( ii ) complexes of tetradentate 4N ligands with diazepane backbones for catalytic olefin epoxidation: effect of nucleophilicity of peroxo complexes on reactivity Saravanan, Natarajan; Sankaralingam, Muniyandi; Palaniandavar, Mallayan RSC Adv., Vol. 4, Issue 23 https://doi.org/10.1039/C3RA44729D	journal	January 2014
A nonheme manganese( iv )–oxo species generated in photocatalytic reaction using water as an oxygen source Wu, Xiujuan; Yang, Xiaonan; Lee, Yong-Min Chemical Communications, Vol. 51, Issue 19 https://doi.org/10.1039/C4CC10411K	journal	January 2015
Redox-inactive metal ions promoted the catalytic reactivity of non-heme manganese complexes towards oxygen atom transfer Choe, Cholho; Yang, Ling; Lv, Zhanao Dalton Transactions, Vol. 44, Issue 19 https://doi.org/10.1039/C4DT03993A	journal	January 2015
Enantioselective aliphatic C–H bond oxidation catalyzed by bioinspired complexes Milan, Michela; Bietti, Massimo; Costas, Miquel Chemical Communications, Vol. 54, Issue 69 https://doi.org/10.1039/C8CC03165G	journal	January 2018
Chiral manganese complexes with pinene appended tetradentate ligands as stereoselective epoxidation catalysts Gómez, Laura; Garcia-Bosch, Isaac; Company, Anna Dalton Transactions, Issue 47 https://doi.org/10.1039/b712754e	journal	January 2007
The unexpected role of pyridine-2-carboxylic acid in manganese based oxidation catalysis with pyridin-2-yl based ligands Pijper, Dirk; Saisaha, Pattama; de Boer, Johannes W. Dalton Transactions, Vol. 39, Issue 43 https://doi.org/10.1039/c0dt00452a	journal	January 2010
Structural characterization of manganese and iron complexes with methylated derivatives of bis(2-pyridylmethyl)-1,2-ethanediamine reveals unanticipated conformational flexibility Coates, Cristina M.; Hagan, Kenton; Mitchell, Casey A. Dalton Transactions, Vol. 40, Issue 16 https://doi.org/10.1039/c0dt01556c	journal	January 2011
Electrochemical formation of MnIII-peroxo complexes supported by pentadentate amino pyridine and imidazole ligands El Ghachtouli, Sanae; Vincent Ching, H. Y.; Lassalle-Kaiser, Benedikt Chemical Communications, Vol. 49, Issue 50 https://doi.org/10.1039/c3cc41300d	journal	January 2013
Reaction landscape of a pentadentate N5-ligated MnII complex with O2˙− and H2O2 includes conversion of a peroxomanganese(iii) adduct to a bis(μ-oxo)dimanganese(iii,iv) species Leto, Domenick F.; Chattopadhyay, Swarup; Day, Victor W. Dalton Transactions, Vol. 42, Issue 36 https://doi.org/10.1039/c3dt51277k	journal	January 2013
Making Fe(BPBP)-catalyzed C–H and CC oxidations more affordable Yazerski, Vital A.; Spannring, Peter; Gatineau, David Organic & Biomolecular Chemistry, Vol. 12, Issue 13 https://doi.org/10.1039/c3ob42249f	journal	January 2014
400. The determination of the paramagnetic susceptibility of substances in solution by nuclear magnetic resonance Evans, D. F. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9590002003	journal	January 1959
Synthetically Useful Reactions of Epoxides Gorzynski Smith, Janice Synthesis, Vol. 1984, Issue 08 https://doi.org/10.1055/s-1984-30921	journal	January 1984
Electron Paramagnetic Resonance of Mn(II) Complexes in Acetonitrile Chan, Sunney I.; Fung, B. M.; Lütje, Hans The Journal of Chemical Physics, Vol. 47, Issue 6 https://doi.org/10.1063/1.1712245	journal	September 1967
1,10-Phenanthroline and 2,2'-bipyridine chelates of higher-valent manganese Goodwin, Ha; Sylva, Rn Australian Journal of Chemistry, Vol. 18, Issue 11 https://doi.org/10.1071/CH9651743	journal	January 1965
OLEX2 : a complete structure solution, refinement and analysis program Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J. Journal of Applied Crystallography, Vol. 42, Issue 2 https://doi.org/10.1107/S0021889808042726	journal	January 2009
Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination Krause, Lennard; Herbst-Irmer, Regine; Sheldrick, George M. Journal of Applied Crystallography, Vol. 48, Issue 1 https://doi.org/10.1107/S1600576714022985	journal	January 2015
Crystal structure refinement with SHELXL Sheldrick, George M. Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8 https://doi.org/10.1107/S2053229614024218	journal	January 2015
SHELXT – Integrated space-group and crystal-structure determination Sheldrick, George M. Acta Crystallographica Section A Foundations and Advances, Vol. 71, Issue 1, p. 3-8 https://doi.org/10.1107/S2053273314026370	journal	January 2015
A Predictably Selective Aliphatic C H Oxidation Reaction for Complex Molecule Synthesis Chen, M. S.; White, M. C. Science, Vol. 318, Issue 5851 https://doi.org/10.1126/science.1148597	journal	November 2007

Similar Records

Manganese Catalysts with Tetradentate N-donor Pyridine-Appended Bipiperidine Ligands for Olefin Epoxidation Reactions: Ligand Electronic Effect and Mechanism

Journal Article · Sun Mar 01 19:00:00 EST 2020 · Catalysts · OSTI ID:2500412

Synthesis of Higher Epoxides by the Joint Catalytic Oxidation of Aldehyde and Olefins

Journal Article · Mon Mar 31 23:00:00 EST 1986 · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) · OSTI ID:7066325

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Alkene epoxidation
Aminopyridine ligands
Manganese(II) complexes

CCDC 1877223: Experimental Crystal Structure Determination Guang, Yang,; A., Mikhalyova, Elena; S., Filatov, Alexander https://doi.org/10.5517/ccdc.csd.cc210dl2 The current record is supplemented by this dataset	dataset	January 2022
CCDC 1877224: Experimental Crystal Structure Determination Guang, Yang,; A., Mikhalyova, Elena; S., Filatov, Alexander https://doi.org/10.5517/ccdc.csd.cc210dm3 The current record is supplemented by this dataset	dataset	January 2022
CCDC 1877225: Experimental Crystal Structure Determination Guang, Yang,; A., Mikhalyova, Elena; S., Filatov, Alexander https://doi.org/10.5517/ccdc.csd.cc210dn4 The current record is supplemented by this dataset	dataset	January 2022
CCDC 1877226: Experimental Crystal Structure Determination Guang, Yang,; A., Mikhalyova, Elena; S., Filatov, Alexander https://doi.org/10.5517/ccdc.csd.cc210dp5 The current record is supplemented by this dataset	dataset	January 2022
CCDC 1877227: Experimental Crystal Structure Determination Guang, Yang,; A., Mikhalyova, Elena; S., Filatov, Alexander https://doi.org/10.5517/ccdc.csd.cc210dq6 The current record is supplemented by this dataset	dataset	January 2022
CCDC 1889822: Experimental Crystal Structure Determination Guang, Yang,; A., Mikhalyova, Elena; S., Filatov, Alexander https://doi.org/10.5517/ccdc.csd.cc21fj01 The current record is supplemented by this dataset	dataset	January 2022

Manganese(II) complexes of 1,1'-bis[(pyridin-2-yl)methyl)]-2,2'-bipiperidine (PYBP): Synthesis, structure, catalytic properties in alkene epoxidation with hydrogen peroxide, and related mechanistic studies

Citation Formats

References (82)

Linked Research (6)

Similar Records

Related Subjects