Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles

doi:10.1021/jacs.7b08678

Title: Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles

Abstract

Activation of dioxygen (O₂) in enzymatic and biomimetic reactions has been intensively investigated over the past several decades. More recently, O–O bond formation, which is the reverse of the O₂-activation reaction, has been the focus of current research. Herein, we report the O₂-activation and O–O bond formation reactions by manganese corrole complexes. In the O₂-activation reaction, Mn(V)-oxo and Mn(IV)-peroxo intermediates were formed when Mn(III) corroles were exposed to O₂ in the presence of base (e.g., OH^–) and hydrogen atom (H atom) donor (e.g., THF or cyclic olefins); the O₂-activation reaction did not occur in the absence of base and H atom donor. Moreover, formation of the Mn(V)-oxo and Mn(IV)-peroxo species was dependent on the amounts of base present in the reaction solution. The role of the base was proposed to lower the oxidation potential of the Mn(III) corroles, thereby facilitating the binding of O₂ and forming a Mn(IV)-superoxo species. The putative Mn(IV)-superoxo species was then converted to the corresponding Mn(IV)-hydroperoxo species by abstracting a H atom from H atom donor, followed by the O–O bond cleavage of the putative Mn(IV)-hydroperoxo species to form a Mn(V)-oxo species. We have also shown that addition of hydroxide ion to the Mn(V)-oxo species affordedmore »« less

Authors:

Guo, Mian ^[1];

^[1]; Gupta, Ranjana ^[1]; Seo, Mi Sook ^[1]; Ohta, Takehiro ^[2]; Wang, Hua-Hua ^[3];

^[3]; Dhuri, Sunder N. ^[4]; Sarangi, Ritimukta ^[5];

^[1];

^[6]

Ewha Womans Univ., Seoul (Korea, Republic of). Dept. of Chemistry and Nano Science
Univ. of Hyogo (Japan). Picobiology Inst. Graduate School of Life Science
South China Univ. of Technology, Guangzhou (China)
Ewha Womans Univ., Seoul (Korea, Republic of). Dept. of Chemistry and Nano Science; Goa Univ. (India). Dept. of Chemistry
SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource
Ewha Womans Univ., Seoul (Korea, Republic of). Dept. of Chemistry and Nano Science; Chinese Academy of Sciences (CAS), Lanzhou (China). State Key Lab. for Oxo Synthesis and Selective Oxidation. Lanzhou Inst. of Chemical Physics

Publication Date:: 2017-10-22

Research Org.:: SLAC National Accelerator Lab., Menlo Park, CA (United States); Ewha Womans Univ., Seoul (Korea, Republic of); Univ. of Hyogo (Japan); South China Univ. of Technology (SCUT), Guangzhou (China)

Sponsoring Org.:: USDOE Office of Science (SC), Biological and Environmental Research (BER); National Inst. of Health (NIH) (United States); National Research Foundation of Korea (NRF); Basic Science Research Program (Korea, Republic of); Ministry of Education, Culture, Sports, Science and Technology (MEXT) (Japan); National Natural Science Foundation of China (NNSFC)

OSTI Identifier:: 1419325

Grant/Contract Number:: AC02-76SF00515; P41GM103393; NRF-2012R1A3A2048842; NRF-2010-00353; 2017R1D1A1B03029982; 2017R1D1A1B03032615; 16H02268; 21371059; 21671068

Resource Type:: Accepted Manuscript

Journal Name:: Journal of the American Chemical Society

Additional Journal Information:: Journal Volume: 139; Journal Issue: 44; Journal ID: ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Guo, Mian, Lee, Yong-Min, Gupta, Ranjana, Seo, Mi Sook, Ohta, Takehiro, Wang, Hua-Hua, Liu, Hai-Yang, Dhuri, Sunder N., Sarangi, Ritimukta, Fukuzumi, Shunichi, and Nam, Wonwoo. Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles.  United States: N. p., 2017. 
        Web.  doi:10.1021/jacs.7b08678.

Copy to clipboard


                    Guo, Mian, Lee, Yong-Min, Gupta, Ranjana, Seo, Mi Sook, Ohta, Takehiro, Wang, Hua-Hua, Liu, Hai-Yang, Dhuri, Sunder N., Sarangi, Ritimukta, Fukuzumi, Shunichi, & Nam, Wonwoo. Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles.  United States.  doi:10.1021/jacs.7b08678.

Copy to clipboard


                    Guo, Mian, Lee, Yong-Min, Gupta, Ranjana, Seo, Mi Sook, Ohta, Takehiro, Wang, Hua-Hua, Liu, Hai-Yang, Dhuri, Sunder N., Sarangi, Ritimukta, Fukuzumi, Shunichi, and Nam, Wonwoo. Sun .  
        "Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles".  United States.  doi:10.1021/jacs.7b08678.  https://www.osti.gov/servlets/purl/1419325.

Copy to clipboard


                    
@article{osti_1419325,

  title        = {Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles},

  author       = {Guo, Mian and Lee, Yong-Min and Gupta, Ranjana and Seo, Mi Sook and Ohta, Takehiro and Wang, Hua-Hua and Liu, Hai-Yang and Dhuri, Sunder N. and Sarangi, Ritimukta and Fukuzumi, Shunichi and Nam, Wonwoo},

  abstractNote = {Activation of dioxygen (O2) in enzymatic and biomimetic reactions has been intensively investigated over the past several decades. More recently, O–O bond formation, which is the reverse of the O2-activation reaction, has been the focus of current research. Herein, we report the O2-activation and O–O bond formation reactions by manganese corrole complexes. In the O2-activation reaction, Mn(V)-oxo and Mn(IV)-peroxo intermediates were formed when Mn(III) corroles were exposed to O2 in the presence of base (e.g., OH–) and hydrogen atom (H atom) donor (e.g., THF or cyclic olefins); the O2-activation reaction did not occur in the absence of base and H atom donor. Moreover, formation of the Mn(V)-oxo and Mn(IV)-peroxo species was dependent on the amounts of base present in the reaction solution. The role of the base was proposed to lower the oxidation potential of the Mn(III) corroles, thereby facilitating the binding of O2 and forming a Mn(IV)-superoxo species. The putative Mn(IV)-superoxo species was then converted to the corresponding Mn(IV)-hydroperoxo species by abstracting a H atom from H atom donor, followed by the O–O bond cleavage of the putative Mn(IV)-hydroperoxo species to form a Mn(V)-oxo species. We have also shown that addition of hydroxide ion to the Mn(V)-oxo species afforded the Mn(IV)-peroxo species via O–O bond formation and the resulting Mn(IV)-peroxo species reverted to the Mn(V)-oxo species upon addition of proton, indicating that the O–O bond formation and cleavage reactions between the Mn(V)-oxo and Mn(IV)-peroxo complexes are reversible. The present paper reports the first example of using the same manganese complex in both O2-activation and O–O bond formation reactions.},

  doi          = {10.1021/jacs.7b08678},

  journal      = {Journal of the American Chemical Society},

  number       = 44,

  volume       = 139,

  place        = {United States},

  year         = {2017},

  month        = {10}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

DOI: 10.1021/jacs.7b08678

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 11 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referencing / citing this record:

An In-Depth Look at the Reactivity of Non-Redox-Metal Alkylperoxides
journal, May 2019

Pietrzak, Tomasz; Justyniak, Iwona; Kubisiak, Marcin
Angewandte Chemie International Edition, Vol. 58, Issue 25
DOI: 10.1002/anie.201904380

A Mn( iv )–peroxo complex in the reactions with proton donors
journal, January 2019

Lee, Chien-Ming; Sankaralingam, Muniyandi; Chuo, Chi-He
Dalton Transactions, Vol. 48, Issue 16
DOI: 10.1039/c9dt00649d

Significantly improved electrocatalytic oxygen reduction by an asymmetrical Pacman dinuclear cobalt( ii ) porphyrin–porphyrin dyad
journal, January 2020

Liu, Yanju; Zhou, Guojun; Zhang, Zongyao
Chemical Science, Vol. 11, Issue 1
DOI: 10.1039/c9sc05041h

An In-Depth Look at the Reactivity of Non-Redox-Metal Alkylperoxides
journal, May 2019

Pietrzak, Tomasz; Justyniak, Iwona; Kubisiak, Marcin
Angewandte Chemie International Edition, Vol. 58, Issue 25
DOI: 10.1002/anie.201904380

A Mn( iv )–peroxo complex in the reactions with proton donors
journal, January 2019

Lee, Chien-Ming; Sankaralingam, Muniyandi; Chuo, Chi-He
Dalton Transactions, Vol. 48, Issue 16
DOI: 10.1039/c9dt00649d

Significantly improved electrocatalytic oxygen reduction by an asymmetrical Pacman dinuclear cobalt( ii ) porphyrin–porphyrin dyad
journal, January 2020

Liu, Yanju; Zhou, Guojun; Zhang, Zongyao
Chemical Science, Vol. 11, Issue 1
DOI: 10.1039/c9sc05041h

An In‐Depth Look at the Reactivity of Non‐Redox‐Metal Alkylperoxides
journal, May 2019

Pietrzak, Tomasz; Justyniak, Iwona; Kubisiak, Marcin
Angewandte Chemie
DOI: 10.1002/ange.201904380

A Corrole‐Based Covalent Organic Framework Featuring Desymmetrized Topology
journal, March 2020

Zhao, Yanming; Dai, Wenhao; Peng, Yunlei
Angewandte Chemie, Vol. 132, Issue 11
DOI: 10.1002/ange.201915569

A Corrole‐Based Covalent Organic Framework Featuring Desymmetrized Topology
journal, February 2020

Zhao, Yanming; Dai, Wenhao; Peng, Yunlei
Angewandte Chemie International Edition, Vol. 59, Issue 11
DOI: 10.1002/anie.201915569

Boosting Molecular Complexity with O ₂ : Iron‐Catalysed Oxygenation of 1‐Arylisochromans through Dehydrogenation, Csp ³ −O Bond Cleavage and Hydrogenolysis
journal, March 2019

Gonzalez‐de‐Castro, Angela; Robertson, Craig M.; Xiao, Jianliang
Chemistry – A European Journal, Vol. 25, Issue 17
DOI: 10.1002/chem.201806117

A mononuclear manganese( iii )–hydroperoxo complex: synthesis by activating dioxygen and reactivity in electrophilic and nucleophilic reactions
journal, January 2018

Sankaralingam, Muniyandi; Lee, Yong-Min; Jeon, So Hyun
Chemical Communications, Vol. 54, Issue 10
DOI: 10.1039/c7cc09492b

The interplay between structural perfectness and CO oxidation catalysis on aluminum, phosphorous and silicon complexes of corroles
journal, January 2019

Mohajeri, Afshan; Hassani, Nasim
Physical Chemistry Chemical Physics, Vol. 21, Issue 14
DOI: 10.1039/c8cp07372d

Kinetics and mechanisms of catalytic water oxidation
journal, January 2019

Fukuzumi, Shunichi; Lee, Yong-Min; Nam, Wonwoo
Dalton Transactions, Vol. 48, Issue 3
DOI: 10.1039/c8dt04341h

Structure and reactivity of the first-row d-block metal-superoxo complexes
journal, January 2019

Fukuzumi, Shunichi; Lee, Yong-Min; Nam, Wonwoo
Dalton Transactions, Vol. 48, Issue 26
DOI: 10.1039/c9dt01402k

A putative heme manganese( v )-oxo species in the C–H activation and epoxidation reactions in an aqueous buffer
journal, January 2019

Harmalkar, Dinesh S.; Santosh, G.; Shetgaonkar, Siddhi B.
New Journal of Chemistry, Vol. 43, Issue 33
DOI: 10.1039/c9nj01381d

Similar Records in DOE PAGES and OSTI.GOV collections:

High-valent manganese–oxo valence tautomers and the influence of Lewis/Brönsted acids on C–H bond cleavage

Journal Article Baglia, Regina A. ; Krest, Courtney M. ; Yang, Tzuhsiung ; ... - Inorganic Chemistry

The addition of Lewis or Brönsted acids (LA = Zn(OTf)₂, B(C₆F₅)₃, HBAr^F, TFA) to the high-valent manganese–oxo complex Mn^V(O)(TBP₈Cz) results in the stabilization of a valence tautomer Mn^IV(O-LA)(TBP₈Cz^•+). The Zn^II and B(C₆F₅)₃ complexes were characterized by manganese K-edge X-ray absorption spectroscopy (XAS). The position of the edge energies and the intensities of the pre-edge (1s to 3d) peaks confirm that the Mn ion is in the +4 oxidation state. Fitting of the extended X-ray absorption fine structure (EXAFS) region reveals 4 N/O ligands at Mn–N_ave = 1.89 Å and a fifth N/O ligand at 1.61 Å, corresponding to the terminalmore »« less
Cited by 5
DOI: 10.1021/acs.inorgchem.6b02109

Full Text Available
Reactivity of a Cobalt(III)–Hydroperoxo Complex in Electrophilic Reactions

Journal Article Shin, Bongki ; Sutherlin, Kyle D. ; Ohta, Takehiro ; ... - Inorganic Chemistry

The reactivity of mononuclear metal-hydroperoxo adducts has fascinated researchers in many areas due to their diverse biological and catalytic processes. In this study, a mononuclear cobalt(III)-peroxo complex bearing a tetradentate macrocyclic ligand, [Co^III(Me₃-TPADP)(O₂)]⁺ (Me₃-TPADP = 3,6,9-trimethyl-3,6,9-triaza-1(2,6)-pyridinacyclodecaphane), was prepared by reacting [Co^II(Me₃-TPADP)(CH₃CN)₂]²⁺ with H₂O₂ in the presence of triethylamine. Upon protonation, the cobalt(III)- peroxo intermediate was converted into a cobalt(III)-hydroperoxo complex, [Co^III(Me₃-TPADP)(O₂H)(CH₃CN)]²⁺. The mononuclear cobalt(III)-peroxo and -hydroperoxo intermediates were characterized by a variety of physicochemical methods. Results of electrospray ionization mass spectrometry clearly show the transformation of the intermediates: the peak at m/z 339.2 assignable to the cobalt(III)-peroxo species disappears withmore »« less
Cited by 10
DOI: 10.1021/acs.inorgchem.6b02288

Full Text Available
Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies

Journal Article Guo, Mian ; Lee, Yong -Min ; Seo, Mi Sook ; ... - Inorganic Chemistry

Mn(III)-iodosylarene porphyrin adducts, [Mn(III)(ArIO)(Porp)]⁺, were synthesized by reacting electron-deficient Mn(III) porphyrin complexes with iodosylarene (ArIO) at –60 °C and characterized using various spectroscopic methods. The [Mn(III)(ArIO)(Porp)]⁺ species were then investigated in the epoxidation of olefins under stoichiometric conditions. In the epoxidation of olefins by the Mn(III)-iodosylarene porphyrin species, epoxide was formed as the sole product with high chemoselectivities and stereoselectivities. For example, cyclohexene oxide was formed exclusively with trace amounts of allylic oxidation products; cis- and trans-stilbenes were oxidized to the corresponding cis- and trans-stilbene oxides, respectively. In the catalytic epoxidation of cyclohexene by an electron-deficient Mn(III) porphyrin complex andmore »« less
DOI: 10.1021/acs.inorgchem.8b01426

Full Text Available
Oxidative cleavage of a phenolic diarylpropane lignin model dimer by manganese peroxidase from Phanerochaete chrysosporium

Journal Article Wariishi, Hiroyuki ; Valli, K ; Gold, M H - Biochemistry; (USA)

In the presence of Mn{sup II} and H{sub 2}O{sub 2}, homogeneous manganese peroxidase oxidized 1-(3,5-dimethoxy-4-hydroxy phenyl)-2- (4-methoxyphenyl)- 1,3-dihydroxypropane (I) to yield 1-(3,5- dimethoxy-4- hydroxyphenyl)-2- (4-methoxyphenyl)-1-oxo-3- hydroxy propane (II), 2,6-dimethoxy- 1,4-benzoquinone (III), 2,6-dimethoxy- 1,4-dihydroxy benzene (IV), 1-(4-methoxyphenyl)- 1-oxo-2-hydroxyethane (V), 1-(4-methoxyphenyl)- 1,2-dihydroxyethane (VI), syringaldehyde (VIII), and 2-(4-methoxyphenyl)- 3-hydroxypropanal (IX). Chemically prepared manganese(III) malonate catalyzed the same reactions. Oxidation of I in H{sub 2}{sup 18}O under argon resulted in >80% incorporation of {sup 18}O into the phenylglycol VI, the hydroquinone IV, and the quinone III. Oxidation of I in H{sub 2}{sup 18}O under aerobic conditions resulted in 40% incorporation of {sup 18}O intomore »« less
DOI: 10.1021/bi00440a044
Insights Into the P-To-Q Conversion in the Catalytic Cycle of Methane Monooxygenase From a Synthetic Model System

Journal Article Xue, G ; Fiedler, A T ; Martinho, M ; ... - Proc. Nat. Acad. Sci. 105:20615,2008

For the catalytic cycle of soluble methane monooxygenase (sMMO), it has been proposed that cleavage of the O-O bond in the ({mu}-peroxo)diiron(III) intermediate P gives rise to the diiron(IV) intermediate Q with an Fe{sub 2}({mu}-O){sub 2} diamond core, which oxidizes methane to methanol. As a model for this conversion, ({mu}-oxo) diiron(III) complex 1 ([Fe{sup III}{sub 2}({mu}-O)({mu}-O{sub 2}H{sub 3})(L){sub 2}]{sup 3+}, L = tris(3,5-dimethyl-4-methoxypyridyl-2-methyl)amine) has been treated consecutively with one eq of H{sub 2}O{sub 2} and one eq of HClO{sub 4} to form 3 ([Fe{sup IV}{sub 2}({mu}-O){sub 2}(L){sub 2}]{sup 4+}). In the course of this reaction a new species, 2, canmore »« less

Similar Records

Title: Dioxygen Activation and O–O Bond Formation Reactions by Manganese Corroles

Abstract

Citation Formats

An In-Depth Look at the Reactivity of Non-Redox-Metal Alkylperoxides journal, May 2019

A Mn( iv )–peroxo complex in the reactions with proton donors journal, January 2019

Significantly improved electrocatalytic oxygen reduction by an asymmetrical Pacman dinuclear cobalt( ii ) porphyrin–porphyrin dyad journal, January 2020

An In-Depth Look at the Reactivity of Non-Redox-Metal Alkylperoxides journal, May 2019

A Mn( iv )–peroxo complex in the reactions with proton donors journal, January 2019

Significantly improved electrocatalytic oxygen reduction by an asymmetrical Pacman dinuclear cobalt( ii ) porphyrin–porphyrin dyad journal, January 2020

An In‐Depth Look at the Reactivity of Non‐Redox‐Metal Alkylperoxides journal, May 2019

A Corrole‐Based Covalent Organic Framework Featuring Desymmetrized Topology journal, March 2020

A Corrole‐Based Covalent Organic Framework Featuring Desymmetrized Topology journal, February 2020

Boosting Molecular Complexity with O 2 : Iron‐Catalysed Oxygenation of 1‐Arylisochromans through Dehydrogenation, Csp 3 −O Bond Cleavage and Hydrogenolysis journal, March 2019

A mononuclear manganese( iii )–hydroperoxo complex: synthesis by activating dioxygen and reactivity in electrophilic and nucleophilic reactions journal, January 2018

The interplay between structural perfectness and CO oxidation catalysis on aluminum, phosphorous and silicon complexes of corroles journal, January 2019

Kinetics and mechanisms of catalytic water oxidation journal, January 2019

Structure and reactivity of the first-row d-block metal-superoxo complexes journal, January 2019

A putative heme manganese( v )-oxo species in the C–H activation and epoxidation reactions in an aqueous buffer journal, January 2019

An In-Depth Look at the Reactivity of Non-Redox-Metal Alkylperoxides
journal, May 2019

A Mn( iv )–peroxo complex in the reactions with proton donors
journal, January 2019

Significantly improved electrocatalytic oxygen reduction by an asymmetrical Pacman dinuclear cobalt( ii ) porphyrin–porphyrin dyad
journal, January 2020

An In-Depth Look at the Reactivity of Non-Redox-Metal Alkylperoxides
journal, May 2019

A Mn( iv )–peroxo complex in the reactions with proton donors
journal, January 2019

Significantly improved electrocatalytic oxygen reduction by an asymmetrical Pacman dinuclear cobalt( ii ) porphyrin–porphyrin dyad
journal, January 2020

An In‐Depth Look at the Reactivity of Non‐Redox‐Metal Alkylperoxides
journal, May 2019

A Corrole‐Based Covalent Organic Framework Featuring Desymmetrized Topology
journal, March 2020

A Corrole‐Based Covalent Organic Framework Featuring Desymmetrized Topology
journal, February 2020

Boosting Molecular Complexity with O ₂ : Iron‐Catalysed Oxygenation of 1‐Arylisochromans through Dehydrogenation, Csp ³ −O Bond Cleavage and Hydrogenolysis
journal, March 2019

A mononuclear manganese( iii )–hydroperoxo complex: synthesis by activating dioxygen and reactivity in electrophilic and nucleophilic reactions
journal, January 2018

The interplay between structural perfectness and CO oxidation catalysis on aluminum, phosphorous and silicon complexes of corroles
journal, January 2019

Kinetics and mechanisms of catalytic water oxidation
journal, January 2019

Structure and reactivity of the first-row d-block metal-superoxo complexes
journal, January 2019

A putative heme manganese( v )-oxo species in the C–H activation and epoxidation reactions in an aqueous buffer
journal, January 2019