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Title: Cobalt(ii) acyl intermediates in carbon–carbon bond formation and oxygenation

Abstract

Tetrahedral cobalt( ii ) hydrocarbyl and CO reversibly form acylcobalt, coupling to give α-hydroxyketone compounds, or oxygenation with O 2 to cobalt( ii ) carboxylates.

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [1]
  1. Iowa State Univ., Ames, IA (United States)
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:
1464488
Alternate Identifier(s):
OSTI ID: 1463748
Report Number(s):
IS-J-9719
Journal ID: ISSN 1477-9226
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Dalton Transactions
Additional Journal Information:
Journal Volume: 47; Journal Issue: 35; Journal ID: ISSN 1477-9226
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. Cobalt(ii) acyl intermediates in carbon–carbon bond formation and oxygenation. United States: N. p., 2018. Web. doi:10.1039/C8DT02661K.
Reinig, Regina R., Fought, Ellie L., Ellern, Arkady, Windus, Theresa L., & Sadow, Aaron D. Cobalt(ii) acyl intermediates in carbon–carbon bond formation and oxygenation. United States. doi:10.1039/C8DT02661K.
Reinig, Regina R., Fought, Ellie L., Ellern, Arkady, Windus, Theresa L., and Sadow, Aaron D. Mon . "Cobalt(ii) acyl intermediates in carbon–carbon bond formation and oxygenation". United States. doi:10.1039/C8DT02661K. https://www.osti.gov/servlets/purl/1464488.
@article{osti_1464488,
title = {Cobalt(ii) acyl intermediates in carbon–carbon bond formation and oxygenation},
author = {Reinig, Regina R. and Fought, Ellie L. and Ellern, Arkady and Windus, Theresa L. and Sadow, Aaron D.},
abstractNote = {Tetrahedral cobalt( ii ) hydrocarbyl and CO reversibly form acylcobalt, coupling to give α-hydroxyketone compounds, or oxygenation with O 2 to cobalt( ii ) carboxylates.},
doi = {10.1039/C8DT02661K},
journal = {Dalton Transactions},
number = 35,
volume = 47,
place = {United States},
year = {2018},
month = {7}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 2 works
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Works referenced in this record:

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NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist
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Thermally stable coordinatively unsaturated alkyl complexes resistant to β-hydride elimination: TpiPrM–CH2CH3 (M = Co, Fe)
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Paramagnetic Alkyl, Hydride, and Alkene Complexes of the Tp t -Bu,Me Co Moiety
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Organometallic Cobalt(II) and Nickel(II) Complexes Supported by Thioether Ligation:  Unexpected Nickel Alkylation by the Borato Ligand Phenyltris(( tert -butylthio)methyl)borate
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    Works referencing / citing this record:

    CCDC 1845866: Experimental Crystal Structure Determination: IFIYEE : butyl-(tris(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenylborate)-cobalt
    dataset, July 2018


    Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen-Coupled Turnover
    journal, June 2004


    Oxidative Carbonylation Reactions: Organometallic Compounds (RM) or Hydrocarbons (RH) as Nucleophiles
    journal, September 2011

    • Liu, Qiang; Zhang, Hua; Lei, Aiwen
    • Angewandte Chemie International Edition, Vol. 50, Issue 46
    • DOI: 10.1002/anie.201100763

    Characterization of the Elusive Rhodizonate Ring-Contraction Decarbonylation C 5 O 4 (OH)CO 2 Me 2− Intermediate to Croconate
    journal, October 2013

    • Lu, Feng; Rheingold, Arnold L.; Miller, Joel S.
    • Chemistry - A European Journal, Vol. 19, Issue 44
    • DOI: 10.1002/chem.201303190

    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

    General atomic and molecular electronic structure system
    journal, November 1993

    • Schmidt, Michael W.; Baldridge, Kim K.; Boatz, Jerry A.
    • Journal of Computational Chemistry, Vol. 14, Issue 11, p. 1347-1363
    • DOI: 10.1002/jcc.540141112

    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

    Structural and spectroscopic models of the A-cluster of acetyl coenzyme a synthase/carbon monoxide dehydrogenase: Nature's Monsanto acetic acid catalyst
    journal, December 2005


    NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations
    journal, September 2010

    • Valiev, M.; Bylaska, E. J.; Govind, N.
    • Computer Physics Communications, Vol. 181, Issue 9, p. 1477-1489
    • DOI: 10.1016/j.cpc.2010.04.018

    Mechanisms of carbon monoxide reduction with zirconium hydrides
    journal, April 1980

    • Wolczanski, Peter T.; Bercaw, John E.
    • Accounts of Chemical Research, Vol. 13, Issue 4
    • DOI: 10.1021/ar50148a004

    Metals and Their Scaffolds To Promote Difficult Enzymatic Reactions
    journal, August 2006


    Coordinatively Saturated Tris(oxazolinyl)borato Zinc Hydride-Catalyzed Cross Dehydrocoupling of Silanes and Alcohols
    journal, May 2011

    • Mukherjee, Debabrata; Thompson, Richard R.; Ellern, Arkady
    • ACS Catalysis, Vol. 1, Issue 7
    • DOI: 10.1021/cs2001016

    Model Complexes of Cobalt-Substituted Matrix Metalloproteinases:  Tools for Inhibitor Design
    journal, September 2006

    • Jacobsen, Faith E.; Breece, Robert M.; Myers, William K.
    • Inorganic Chemistry, Vol. 45, Issue 18
    • DOI: 10.1021/ic060901u

    Relativistic and correlation effects for element 105 (hahnium, Ha): a comparative study of M and MO (M = Nb, Ta, Ha) using energy-adjusted ab initio pseudopotentials
    journal, June 1993

    • Dolg, Michael; Stoll, Hermann; Preuss, Heinzwerner
    • The Journal of Physical Chemistry, Vol. 97, Issue 22
    • DOI: 10.1021/j100124a012

    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

    Concerted C−N and C−H Bond Formation in a Magnesium-Catalyzed Hydroamination
    journal, December 2010

    • Dunne, James F.; Fulton, D. Bruce; Ellern, Arkady
    • Journal of the American Chemical Society, Vol. 132, Issue 50
    • DOI: 10.1021/ja108881s

    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

    Synthesis of .alpha.-hydroxy ketones by direct, low-temperature, in situ nucleophilic acylation of aldehydes and ketones by acyllithium reagents
    journal, October 1992

    • Seyferth, Dietmar; Weinstein, Robert M.; Hui, Richard C.
    • The Journal of Organic Chemistry, Vol. 57, Issue 21
    • DOI: 10.1021/jo00047a014

    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

    NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist
    journal, May 2010

    • Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H.
    • Organometallics, Vol. 29, Issue 9
    • DOI: 10.1021/om100106e

    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

    Spin Crossover during β-Hydride Elimination in High-Spin Iron(II)– and Cobalt(II)–Alkyl Complexes
    journal, August 2013

    • Bellows, Sarina M.; Cundari, Thomas R.; Holland, Patrick L.
    • Organometallics, Vol. 32, Issue 17
    • DOI: 10.1021/om400325x

    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

    Molecular cobalt electrocatalyst for proton reduction at low overpotential
    journal, January 2014

    • Ahn, Hyun S.; Davenport, Timothy C.; Tilley, T. Don
    • Chemical Communications, Vol. 50, Issue 29
    • DOI: 10.1039/c3cc49682a

    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

    Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions
    journal, January 1980

    • Krishnan, R.; Binkley, J. S.; Seeger, R.
    • The Journal of Chemical Physics, Vol. 72, Issue 1
    • DOI: 10.1063/1.438955

    Rationale for mixing exact exchange with density functional approximations
    journal, December 1996

    • Perdew, John P.; Ernzerhof, Matthias; Burke, Kieron
    • The Journal of Chemical Physics, Vol. 105, Issue 22, p. 9982-9985
    • DOI: 10.1063/1.472933