skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Rapid and ordered carbonylation and oxygenation of a cobalt(II) methyl

Abstract

To MCoMe reacts rapidly with CO to give a low spin To MCo{C(O)Me}CO species, which is selectively oxygenated to form To MCoOAc.

Authors:
 [1];  [1];  [2];  [1]; ORCiD logo [1]
  1. Iowa State Univ., Ames, IA (United States). Dept. of Chemistry; Ames Lab., Ames, IA (United States)
  2. Iowa State Univ., Ames, IA (United States). Dept. of Chemistry
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1394815
Report Number(s):
IS-J-9445
Journal ID: ISSN 1359-7345; CHCOFS
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
ChemComm
Additional Journal Information:
Journal Volume: 53; Journal Issue: 80; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Reinig, Regina R., Fought, Ellie L., Ellern, Arkady, Windus, Theresa L., and Sadow, Aaron D. Rapid and ordered carbonylation and oxygenation of a cobalt(II) methyl. United States: N. p., 2017. Web. doi:10.1039/C7CC06339C.
Reinig, Regina R., Fought, Ellie L., Ellern, Arkady, Windus, Theresa L., & Sadow, Aaron D. Rapid and ordered carbonylation and oxygenation of a cobalt(II) methyl. United States. doi:10.1039/C7CC06339C.
Reinig, Regina R., Fought, Ellie L., Ellern, Arkady, Windus, Theresa L., and Sadow, Aaron D. Fri . "Rapid and ordered carbonylation and oxygenation of a cobalt(II) methyl". United States. doi:10.1039/C7CC06339C. https://www.osti.gov/servlets/purl/1394815.
@article{osti_1394815,
title = {Rapid and ordered carbonylation and oxygenation of a cobalt(II) methyl},
author = {Reinig, Regina R. and Fought, Ellie L. and Ellern, Arkady and Windus, Theresa L. and Sadow, Aaron D.},
abstractNote = {ToMCoMe reacts rapidly with CO to give a low spin ToMCo{C(O)Me}CO species, which is selectively oxygenated to form ToMCoOAc.},
doi = {10.1039/C7CC06339C},
journal = {ChemComm},
number = 80,
volume = 53,
place = {United States},
year = {2017},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 2 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Acetogenesis and the Wood–Ljungdahl pathway of CO2 fixation
journal, December 2008

  • Ragsdale, Stephen W.; Pierce, Elizabeth
  • Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1784, Issue 12, p. 1873-1898
  • DOI: 10.1016/j.bbapap.2008.08.012

Structures, Physicochemical Properties, and Reactivities of Cobalt(II) Complexes Supported by a Homoscorpionate (Tris(pyrazolyl)borate) Ligand Tp Ph,Me
journal, December 2011

  • Kunishita, Atsushi; Gianetti, Thomas L.; Arnold, John
  • Organometallics, Vol. 31, Issue 1
  • DOI: 10.1021/om200973x

Acetyl-coenzyme A synthase: the case for a Nip0-based mechanism of catalysis
journal, June 2004


Elucidation of a Low Spin Cobalt(II) System in a Distorted Tetrahedral Geometry
journal, December 2002

  • Jenkins, David M.; Di Bilio, Angel J.; Allen, Matthew J.
  • Journal of the American Chemical Society, Vol. 124, Issue 51
  • DOI: 10.1021/ja026433e

Thermally stable coordinatively unsaturated alkyl complexes resistant to β-hydride elimination: TpiPrM–CH2CH3 (M = Co, Fe)
journal, January 1999

  • Shirasawa, Nobuhiko; Akita, Munetaka; Hikichi, Shiro
  • Chemical Communications, Issue 5
  • DOI: 10.1039/a809441a

High-Spin Organocobalt(II) Complexes in a Thioether Coordination Environment
journal, February 2007

  • DuPont, Julie A.; Coxey, Michael B.; Schebler, Peter J.
  • Organometallics, Vol. 26, Issue 4
  • DOI: 10.1021/om0608253

Aliphatic C−H Bond Oxygenation by the Co II OOX Species with the Hindered Hydrotris(pyrazolyl)borate Ligand (X = Co(II), Alkyl, H)
journal, May 1998

  • Hikichi, Shiro; Komatsuzaki, Hidehito; Akita, Munetaka
  • Journal of the American Chemical Society, Vol. 120, Issue 19
  • DOI: 10.1021/ja9720523

Paramagnetic Alkyl, Hydride, and Alkene Complexes of the Tp t -Bu,Me Co Moiety
journal, February 1999

  • Jewson, Jennifer D.; Liable-Sands, Louise M.; Yap, Glenn P. A.
  • Organometallics, Vol. 18, Issue 3
  • DOI: 10.1021/om980844f

Organometallic Cobalt(II) and Nickel(II) Complexes Supported by Thioether Ligation:  Unexpected Nickel Alkylation by the Borato Ligand Phenyltris(( tert -butylthio)methyl)borate
journal, January 2001

  • Schebler, Peter J.; Mandimutsira, Beaven S.; Riordan, Charles G.
  • Journal of the American Chemical Society, Vol. 123, Issue 2
  • DOI: 10.1021/ja002638g

Synthesis and Oxidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates: Synthesis and Oxidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates
journal, April 2016

  • Reinig, Regina R.; Mukherjee, Debabrata; Weinstein, Zachary B.
  • European Journal of Inorganic Chemistry, Vol. 2016, Issue 15-16
  • DOI: 10.1002/ejic.201600237

Geometry and Spin Change at the Heart of a Cobalt(II) Complex: A Special Case of Solvatomorphism
journal, April 2015

  • Cibian, Mihaela; Hanan, Garry S.
  • Chemistry - A European Journal, Vol. 21, Issue 26
  • DOI: 10.1002/chem.201500852

Removing the Sting from the Tail:  Reversible Protonation of Scorpionate Ligands in Cobalt(II) Tris(carbene)borate Complexes
journal, November 2006

  • Cowley, Ryan E.; Bontchev, Ranko P.; Duesler, Eileen N.
  • Inorganic Chemistry, Vol. 45, Issue 24
  • DOI: 10.1021/ic061299a

Can Spin State Change Slow Organometallic Reactions?
journal, November 1995

  • Detrich, Jennifer L.; Reinaud, Olivia M.; Rheingold, Arnold L.
  • Journal of the American Chemical Society, Vol. 117, Issue 47
  • DOI: 10.1021/ja00152a015

Characterization of nickel( ii )-acylperoxo species relevant to catalytic alkanehydroxylation by nickel complex with mCPBA
journal, January 2013

  • Hikichi, Shiro; Hanaue, Kento; Fujimura, Takako
  • Dalton Trans., Vol. 42, Issue 10
  • DOI: 10.1039/C2DT32419A

Remarkably Robust Monomeric Alkylperoxyzinc Compounds from Tris(oxazolinyl)boratozinc Alkyls and O 2
journal, July 2012

  • Mukherjee, Debabrata; Ellern, Arkady; Sadow, Aaron D.
  • Journal of the American Chemical Society, Vol. 134, Issue 31
  • DOI: 10.1021/ja303440n

Structural Distortion of the TpCo-L Fragment (Tp = tris(pyrazolyl)borate). Analysis by X-ray Diffraction and Density Functional Theory
journal, January 1996

  • Detrich, Jennifer L.; Konečný, Robert; Vetter, William M.
  • Journal of the American Chemical Society, Vol. 118, Issue 7
  • DOI: 10.1021/ja9523101

Transition Metal-Catalyzed Oxidative Carbonylation of Amines to Ureas
journal, September 2007

  • Díaz, Delmy J.; Darko, Ampofo K.; McElwee-White, Lisa
  • European Journal of Organic Chemistry, Vol. 2007, Issue 27
  • DOI: 10.1002/ejoc.200700148

Iron, cobalt, and nickel complexes having anomalous magnetic moments
journal, January 1968

  • Barefield, E. Kent; Busch, D. H.; Nelson, S. M.
  • Quarterly Reviews, Chemical Society, Vol. 22, Issue 4
  • DOI: 10.1039/qr9682200457

    Works referencing / citing this record:

    CCDC 1564301: Experimental Crystal Structure Determination: HEJRUM : (phenyl tris(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)borate)-methyl-cobalt(ii)
    dataset, July 2017


    Geometry and Spin Change at the Heart of a Cobalt(II) Complex: A Special Case of Solvatomorphism
    journal, April 2015

    • Cibian, Mihaela; Hanan, Garry S.
    • Chemistry - A European Journal, Vol. 21, Issue 26
    • DOI: 10.1002/chem.201500852

    Synthesis and Oxidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates: Synthesis and Oxidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates
    journal, April 2016

    • Reinig, Regina R.; Mukherjee, Debabrata; Weinstein, Zachary B.
    • European Journal of Inorganic Chemistry, Vol. 2016, Issue 15-16
    • DOI: 10.1002/ejic.201600237

    Transition Metal-Catalyzed Oxidative Carbonylation of Amines to Ureas
    journal, September 2007

    • Díaz, Delmy J.; Darko, Ampofo K.; McElwee-White, Lisa
    • European Journal of Organic Chemistry, Vol. 2007, Issue 27
    • DOI: 10.1002/ejoc.200700148

    Acetyl-coenzyme A synthase: the case for a Nip0-based mechanism of catalysis
    journal, June 2004


    Acetogenesis and the Wood–Ljungdahl pathway of CO2 fixation
    journal, December 2008

    • Ragsdale, Stephen W.; Pierce, Elizabeth
    • Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1784, Issue 12, p. 1873-1898
    • DOI: 10.1016/j.bbapap.2008.08.012

    Removing the Sting from the Tail:  Reversible Protonation of Scorpionate Ligands in Cobalt(II) Tris(carbene)borate Complexes
    journal, November 2006

    • Cowley, Ryan E.; Bontchev, Ranko P.; Duesler, Eileen N.
    • Inorganic Chemistry, Vol. 45, Issue 24
    • DOI: 10.1021/ic061299a

    Can Spin State Change Slow Organometallic Reactions?
    journal, November 1995

    • Detrich, Jennifer L.; Reinaud, Olivia M.; Rheingold, Arnold L.
    • Journal of the American Chemical Society, Vol. 117, Issue 47
    • DOI: 10.1021/ja00152a015

    Organometallic Cobalt(II) and Nickel(II) Complexes Supported by Thioether Ligation:  Unexpected Nickel Alkylation by the Borato Ligand Phenyltris(( tert -butylthio)methyl)borate
    journal, January 2001

    • Schebler, Peter J.; Mandimutsira, Beaven S.; Riordan, Charles G.
    • Journal of the American Chemical Society, Vol. 123, Issue 2
    • DOI: 10.1021/ja002638g

    Elucidation of a Low Spin Cobalt(II) System in a Distorted Tetrahedral Geometry
    journal, December 2002

    • Jenkins, David M.; Di Bilio, Angel J.; Allen, Matthew J.
    • Journal of the American Chemical Society, Vol. 124, Issue 51
    • DOI: 10.1021/ja026433e

    Remarkably Robust Monomeric Alkylperoxyzinc Compounds from Tris(oxazolinyl)boratozinc Alkyls and O 2
    journal, July 2012

    • Mukherjee, Debabrata; Ellern, Arkady; Sadow, Aaron D.
    • Journal of the American Chemical Society, Vol. 134, Issue 31
    • DOI: 10.1021/ja303440n

    Structural Distortion of the TpCo-L Fragment (Tp = tris(pyrazolyl)borate). Analysis by X-ray Diffraction and Density Functional Theory
    journal, January 1996

    • Detrich, Jennifer L.; Konečný, Robert; Vetter, William M.
    • Journal of the American Chemical Society, Vol. 118, Issue 7
    • DOI: 10.1021/ja9523101

    Aliphatic C−H Bond Oxygenation by the Co II OOX Species with the Hindered Hydrotris(pyrazolyl)borate Ligand (X = Co(II), Alkyl, H)
    journal, May 1998

    • Hikichi, Shiro; Komatsuzaki, Hidehito; Akita, Munetaka
    • Journal of the American Chemical Society, Vol. 120, Issue 19
    • DOI: 10.1021/ja9720523

    High-Spin Organocobalt(II) Complexes in a Thioether Coordination Environment
    journal, February 2007

    • DuPont, Julie A.; Coxey, Michael B.; Schebler, Peter J.
    • Organometallics, Vol. 26, Issue 4
    • DOI: 10.1021/om0608253

    Structures, Physicochemical Properties, and Reactivities of Cobalt(II) Complexes Supported by a Homoscorpionate (Tris(pyrazolyl)borate) Ligand Tp Ph,Me
    journal, December 2011

    • Kunishita, Atsushi; Gianetti, Thomas L.; Arnold, John
    • Organometallics, Vol. 31, Issue 1
    • DOI: 10.1021/om200973x

    Paramagnetic Alkyl, Hydride, and Alkene Complexes of the Tp t -Bu,Me Co Moiety
    journal, February 1999

    • Jewson, Jennifer D.; Liable-Sands, Louise M.; Yap, Glenn P. A.
    • Organometallics, Vol. 18, Issue 3
    • DOI: 10.1021/om980844f

    Thermally stable coordinatively unsaturated alkyl complexes resistant to β-hydride elimination: TpiPrM–CH2CH3 (M = Co, Fe)
    journal, January 1999

    • Shirasawa, Nobuhiko; Akita, Munetaka; Hikichi, Shiro
    • Chemical Communications, Issue 5
    • DOI: 10.1039/a809441a

    Cobalt( ii ) acyl intermediates in carbon–carbon bond formation and oxygenation
    journal, January 2018

    • Reinig, Regina R.; Fought, Ellie L.; Ellern, Arkady
    • Dalton Transactions, Vol. 47, Issue 35
    • DOI: 10.1039/c8dt02661k

    Iron, cobalt, and nickel complexes having anomalous magnetic moments
    journal, January 1968

    • Barefield, E. Kent; Busch, D. H.; Nelson, S. M.
    • Quarterly Reviews, Chemical Society, Vol. 22, Issue 4
    • DOI: 10.1039/qr9682200457

    Cobalt( ii ) acyl intermediates in carbon–carbon bond formation and oxygenation
    journal, January 2018

    • Reinig, Regina R.; Fought, Ellie L.; Ellern, Arkady
    • Dalton Transactions, Vol. 47, Issue 35
    • DOI: 10.1039/c8dt02661k