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Title: [NiIII(OMe)]-mediated reductive activation of CO2 affording a Ni(κ1-OCO) complex

Abstract

Here, carbon dioxide is expected to be employed as an inexpensive and potential feedstock of C1 sources for the mass production of valuable chemicals and fuel. Versatile chemical transformations of CO2, i.e. insertion of CO2 producing bicarbonate/acetate/formate, cleavage of CO2 yielding μ-CO/μ-oxo transition-metal complexes, and electrocatalytic reduction of CO2 affording CO/HCOOH/CH3OH/CH4/C2H4/oxalate were well documented. Herein, we report a novel pathway for the reductive activation of CO2 by the [NiIII(OMe)(P(C6H3-3-SiMe3-2-S)3)] complex, yielding the [NiIII1-OCO˙)(P(C6H3-3-SiMe3-2-S)3)] complex. The formation of this unusual NiIII1-OCO˙–) complex was characterized by single-crystal X-ray diffraction, EPR, IR, SQUID, Ni/S K-edge X-ray absorption spectroscopy, and Ni valence-to-core X-ray emission spectroscopy. The inertness of the analogous complexes [NiIII(SPh)], [NiII(CO)], and [NiII(N2H4)] toward CO2, in contrast, demonstrates that the ionic [NiIII(OMe)] core attracts the binding of weak σ-donor CO2 and triggers the subsequent reduction of CO2 by the nucleophilic [OMe] in the immediate vicinity. This metal–ligand cooperative activation of CO2 may open a novel pathway promoting the subsequent incorporation of CO2 in the buildup of functionalized products.

Authors:
 [1];  [1];  [2];  [3];  [3];  [1];  [4];  [5];  [5];  [1]
  1. National Tsing Hua Univ., Hsinchu (Taiwan)
  2. Chung Yuan Christian Univ., Taoyuan (Taiwan)
  3. SLAC National Accelerator Lab., Menlo Park, CA (United States)
  4. National Taiwan Normal Univ., Taipei (Taiwan)
  5. National Synchrotron Radiation Research Center, Hsinchu (Taiwan)
Publication Date:
Research Org.:
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1251399
Grant/Contract Number:  
AC02-76SF00515
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 1021; Journal Issue: C; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Chiou, Tzung -Wen, Tseng, Yen -Ming, Lu, Tsai -Te, Weng, Tsu -Chien, Sokaras, Dimosthenes, Ho, Wei -Chieh, Kuo, Ting -Shen, Jang, Ling -Yun, Lee, Jyh -Fu, and Liaw, Wen -Feng. [NiIII(OMe)]-mediated reductive activation of CO2 affording a Ni(κ1-OCO) complex. United States: N. p., 2016. Web. doi:10.1039/C5SC04652A.
Chiou, Tzung -Wen, Tseng, Yen -Ming, Lu, Tsai -Te, Weng, Tsu -Chien, Sokaras, Dimosthenes, Ho, Wei -Chieh, Kuo, Ting -Shen, Jang, Ling -Yun, Lee, Jyh -Fu, & Liaw, Wen -Feng. [NiIII(OMe)]-mediated reductive activation of CO2 affording a Ni(κ1-OCO) complex. United States. doi:10.1039/C5SC04652A.
Chiou, Tzung -Wen, Tseng, Yen -Ming, Lu, Tsai -Te, Weng, Tsu -Chien, Sokaras, Dimosthenes, Ho, Wei -Chieh, Kuo, Ting -Shen, Jang, Ling -Yun, Lee, Jyh -Fu, and Liaw, Wen -Feng. Wed . "[NiIII(OMe)]-mediated reductive activation of CO2 affording a Ni(κ1-OCO) complex". United States. doi:10.1039/C5SC04652A. https://www.osti.gov/servlets/purl/1251399.
@article{osti_1251399,
title = {[NiIII(OMe)]-mediated reductive activation of CO2 affording a Ni(κ1-OCO) complex},
author = {Chiou, Tzung -Wen and Tseng, Yen -Ming and Lu, Tsai -Te and Weng, Tsu -Chien and Sokaras, Dimosthenes and Ho, Wei -Chieh and Kuo, Ting -Shen and Jang, Ling -Yun and Lee, Jyh -Fu and Liaw, Wen -Feng},
abstractNote = {Here, carbon dioxide is expected to be employed as an inexpensive and potential feedstock of C1 sources for the mass production of valuable chemicals and fuel. Versatile chemical transformations of CO2, i.e. insertion of CO2 producing bicarbonate/acetate/formate, cleavage of CO2 yielding μ-CO/μ-oxo transition-metal complexes, and electrocatalytic reduction of CO2 affording CO/HCOOH/CH3OH/CH4/C2H4/oxalate were well documented. Herein, we report a novel pathway for the reductive activation of CO2 by the [NiIII(OMe)(P(C6H3-3-SiMe3-2-S)3)]– complex, yielding the [NiIII(κ1-OCO˙–)(P(C6H3-3-SiMe3-2-S)3)]– complex. The formation of this unusual NiIII(κ1-OCO˙–) complex was characterized by single-crystal X-ray diffraction, EPR, IR, SQUID, Ni/S K-edge X-ray absorption spectroscopy, and Ni valence-to-core X-ray emission spectroscopy. The inertness of the analogous complexes [NiIII(SPh)], [NiII(CO)], and [NiII(N2H4)] toward CO2, in contrast, demonstrates that the ionic [NiIII(OMe)] core attracts the binding of weak σ-donor CO2 and triggers the subsequent reduction of CO2 by the nucleophilic [OMe]– in the immediate vicinity. This metal–ligand cooperative activation of CO2 may open a novel pathway promoting the subsequent incorporation of CO2 in the buildup of functionalized products.},
doi = {10.1039/C5SC04652A},
journal = {Chemical Science},
number = C,
volume = 1021,
place = {United States},
year = {2016},
month = {2}
}

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Works referenced in this record:

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Differential Reduction of CO 2 by Molybdenum and Vanadium Nitrogenases
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  • Angewandte Chemie, Vol. 126, Issue 43
  • DOI: 10.1002/ange.201406863

    Works referencing / citing this record:

    Efficient Fixation of Carbon Dioxide by Hypervalent Organobismuth Oxide, Hydroxide, and Alkoxide
    journal, August 2008

    • Yin, Shuang-Feng; Maruyama, Junpei; Yamashita, Takashi
    • Angewandte Chemie International Edition, Vol. 47, Issue 35
    • DOI: 10.1002/anie.200802277

    Differential Reduction of CO 2 by Molybdenum and Vanadium Nitrogenases
    journal, September 2014

    • Rebelein, Johannes G.; Hu, Yilin; Ribbe, Markus W.
    • Angewandte Chemie International Edition, Vol. 53, Issue 43
    • DOI: 10.1002/anie.201406863

    How the [NiFe 4 S 4 ] Cluster of CO Dehydrogenase Activates CO 2 and NCO
    journal, April 2015

    • Fesseler, Jochen; Jeoung, Jae-Hun; Dobbek, Holger
    • Angewandte Chemie International Edition, Vol. 54, Issue 29
    • DOI: 10.1002/anie.201501778

    A Biomimetic Nickel Complex with a Reduced CO 2 Ligand Generated by Formate Deprotonation and Its Behaviour towards CO 2
    journal, May 2018

    • Zimmermann, Philipp; Hoof, Santina; Braun-Cula, Beatrice
    • Angewandte Chemie International Edition, Vol. 57, Issue 24
    • DOI: 10.1002/anie.201802655

    Ligand K-edge X-ray absorption spectroscopy: covalency of ligand–metal bonds
    journal, January 2005

    • Solomon, Edward I.; Hedman, Britt; Hodgson, Keith O.
    • Coordination Chemistry Reviews, Vol. 249, Issue 1-2
    • DOI: 10.1016/j.ccr.2004.03.020

    Recent developments in the activation of carbon dioxide by metal complexes
    journal, January 1999


    Transformation of Carbon Dioxide
    journal, June 2007

    • Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki
    • Chemical Reviews, Vol. 107, Issue 6
    • DOI: 10.1021/cr068357u

    Structure, Function, and Mechanism of the Nickel Metalloenzymes, CO Dehydrogenase, and Acetyl-CoA Synthase
    journal, February 2014

    • Can, Mehmet; Armstrong, Fraser A.; Ragsdale, Stephen W.
    • Chemical Reviews, Vol. 114, Issue 8
    • DOI: 10.1021/cr400461p

    Electronic spectoscopy of isoelectronic molecules. II. Linear triatomic groupings containing sixteen valence electrons
    journal, February 1971

    • McGlynn, Sean P.; Rabalais, John W.; McDonald, Jimmie R.
    • Chemical Reviews, Vol. 71, Issue 1
    • DOI: 10.1021/cr60269a004

    The Organometallic Chemistry of Carbon Dioxide
    journal, January 1996


    The impact of Metal–Ligand Cooperation in Hydrogenation of Carbon Dioxide Catalyzed by Ruthenium PNP Pincer
    journal, October 2013

    • Filonenko, Georgy A.; Conley, Matthew P.; Copéret, Christophe
    • ACS Catalysis, Vol. 3, Issue 11
    • DOI: 10.1021/cs4006869

    Reactions of CO 2 and CS 2 with 1,2-Bis(di- tert -butylphosphino)ethane Complexes of Nickel(0) and Nickel(I)
    journal, November 2010

    • Anderson, John S.; Iluc, Vlad M.; Hillhouse, Gregory L.
    • Inorganic Chemistry, Vol. 49, Issue 21
    • DOI: 10.1021/ic101652e

    O/C Bond Cleavage of CO 2 by Ni I
    journal, March 2008

    • Fullmer, Benjamin C.; Fan, Hongjun; Pink, Maren
    • Inorganic Chemistry, Vol. 47, Issue 6
    • DOI: 10.1021/ic701843u

    Organosamarium-Mediated Transformations of CO 2 and COS:  Monoinsertion and Disproportionation Reactions and the Reductive Coupling of CO 2 to [O 2 CCO 2 ] 2-
    journal, February 1998

    • Evans, William J.; Seibel, Christopher A.; Ziller, Joseph W.
    • Inorganic Chemistry, Vol. 37, Issue 4
    • DOI: 10.1021/ic971381t

    Formation of CO 2 - Radical Ions When CO 2 is Adsorbed on Irradiated Magnesium Oxide
    journal, July 1965

    • Lunsford, Jack H.; Jayne, John P.
    • The Journal of Physical Chemistry, Vol. 69, Issue 7
    • DOI: 10.1021/j100891a006

    Tris(pyrazolyl)hydroboratozinc hydroxide complexes as functional models for carbonic anhydrase: on the nature of the bicarbonate intermediate
    journal, June 1993

    • Looney, Adrian; Han, Runyu; McNeill, Kristopher
    • Journal of the American Chemical Society, Vol. 115, Issue 11
    • DOI: 10.1021/ja00064a033

    Mononuclear Nickel(III) and Nickel(II) Thiolate Complexes with Intramolecular S−H Proton Interacting with Both Sulfur and Nickel:  Relevance to the [NiFe]/[NiFeSe] Hydrogenases
    journal, July 2004

    • Lee, Chien-Ming; Chen, Chien-Hong; Ke, Shyue-Chu
    • Journal of the American Chemical Society, Vol. 126, Issue 27
    • DOI: 10.1021/ja048568l

    Carbon Dioxide Reduction and Carbon Monoxide Activation Employing a Reactive Uranium(III) Complex
    journal, August 2005

    • Castro-Rodriguez, Ingrid; Meyer, Karsten
    • Journal of the American Chemical Society, Vol. 127, Issue 32
    • DOI: 10.1021/ja053497r

    Fe(I)-Mediated Reductive Cleavage and Coupling of CO 2 :  An Fe II (μ-O,μ-CO)Fe II Core
    journal, January 2007

    • Lu, Connie C.; Saouma, Caroline T.; Day, Michael W.
    • Journal of the American Chemical Society, Vol. 129, Issue 1
    • DOI: 10.1021/ja065524z

    Phosphinite-Ni(0) Mediated Formation of a Phosphide-Ni(II)-OCOOMe Species via Uncommon Metal–Ligand Cooperation
    journal, March 2015

    • Kim, Yeong-Eun; Oh, Seohee; Kim, Seji
    • Journal of the American Chemical Society, Vol. 137, Issue 13
    • DOI: 10.1021/ja513112r

    Oxygen-Atom Transfer from Carbon Dioxide to a Fischer Carbene at (PNP)Ir
    journal, May 2008

    • Whited, Matthew T.; Grubbs, Robert H.
    • Journal of the American Chemical Society, Vol. 130, Issue 18
    • DOI: 10.1021/ja801865c

    Carbon Dioxide Activation with Sterically Pressured Mid- and High-Valent Uranium Complexes
    journal, September 2008

    • Bart, Suzanne C.; Anthon, Christian; Heinemann, Frank W.
    • Journal of the American Chemical Society, Vol. 130, Issue 37
    • DOI: 10.1021/ja804263w

    A Germanium(II) Hydride as an Effective Reagent for Hydrogermylation Reactions
    journal, January 2009

    • Jana, Anukul; Ghoshal, Debajyoti; Roesky, Herbert W.
    • Journal of the American Chemical Society, Vol. 131, Issue 3
    • DOI: 10.1021/ja808656t

    Iron-Catalyzed Reduction of CO 2 into Methylene: Formation of C–N, C–O, and C–C Bonds
    journal, July 2015

    • Jin, Guanghua; Werncke, C. Gunnar; Escudié, Yannick
    • Journal of the American Chemical Society, Vol. 137, Issue 30
    • DOI: 10.1021/jacs.5b06077

    Radical Scavenging of White Tea and Its Flavonoid Constituents by Electron Paramagnetic Resonance (EPR) Spectroscopy
    journal, June 2014

    • Azman, Nurul A. M.; Peiró, Sara; Fajarí, Lluís
    • Journal of Agricultural and Food Chemistry, Vol. 62, Issue 25
    • DOI: 10.1021/jf501707p

    Addition of CO 2 to Alkyl Iron Complexes, Fe(PP) 2 Me 2
    journal, May 2008

    • Allen, Olivia R.; Dalgarno, Scott J.; Field, Leslie D.
    • Organometallics, Vol. 27, Issue 9
    • DOI: 10.1021/om800091a

    Utilisation of CO2 as a chemical feedstock: opportunities and challenges
    journal, January 2007

    • Aresta, Michele; Dibenedetto, Angela
    • Dalton Transactions, Issue 28
    • DOI: 10.1039/b700658f

    Catalysis of the electrochemical reduction of carbon dioxide
    journal, January 2013

    • Costentin, Cyrille; Robert, Marc; Savéant, Jean-Michel
    • Chem. Soc. Rev., Vol. 42, Issue 6
    • DOI: 10.1039/c2cs35360a

    New nickel–carbon dioxide complex: synthesis, properties, and crystallographic characterization of (carbon dioxide)-bis(tricyclohexylphosphine)nickel
    journal, January 1975

    • Aresta, Michele; Nobile, C. Francesco; Albano, Vincenzo G.
    • J. Chem. Soc., Chem. Commun., Vol. 0, Issue 15
    • DOI: 10.1039/c39750000636

    Formation of a nickel carbon dioxide adduct and its transformation mediated by a Lewis acid
    journal, January 2014

    • Kim, Yeong-Eun; Kim, Jin; Lee, Yunho
    • Chem. Commun., Vol. 50, Issue 78
    • DOI: 10.1039/c4cc04800h

    Reversible CO 2 binding triggered by metal–ligand cooperation in a rhenium( i ) PNP pincer-type complex and the reaction with dihydrogen
    journal, January 2014

    • Vogt, Matthias; Nerush, Alexander; Diskin-Posner, Yael
    • Chem. Sci., Vol. 5, Issue 5
    • DOI: 10.1039/c4sc00130c

    A Linear, O-Coordinated  1-CO2 Bound to Uranium
    journal, September 2004


    Carbon Dioxide Activation at the Ni,Fe-Cluster of Anaerobic Carbon Monoxide Dehydrogenase
    journal, November 2007


    Electrocatalytic CO2 Conversion to Oxalate by a Copper Complex
    journal, January 2010


    A Biomimetic Nickel Complex with a Reduced CO 2 Ligand Generated by Formate Deprotonation and Its Behaviour towards CO 2
    journal, May 2018

    • Zimmermann, Philipp; Hoof, Santina; Braun-Cula, Beatrice
    • Angewandte Chemie International Edition, Vol. 57, Issue 24
    • DOI: 10.1002/anie.201802655

    Ein biomimetischer Nickelkomplex mit einem reduzierten, durch Formiatdeprotonierung erzeugten CO 2 -Liganden und sein Verhalten gegenüber CO 2
    journal, May 2018

    • Zimmermann, Philipp; Hoof, Santina; Braun-Cula, Beatrice
    • Angewandte Chemie, Vol. 130, Issue 24
    • DOI: 10.1002/ange.201802655

    XANES/EPR Evidence of the Oxidation of Nickel(II) Quinolinylpropioamide and Its Application in Csp 3 −H Functionalization
    journal, March 2019

    • Hao, Wenyan; Sha, Yuchen; Deng, Yi
    • Chemistry – A European Journal, Vol. 25, Issue 19
    • DOI: 10.1002/chem.201900009