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


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

 [1];  [1];  [1];  [1]; ORCiD logo [1]
  1. Iowa State Univ., Ames, IA (United States)
Publication Date:
Research Org.:
Ames Lab., Ames, IA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
Alternate Identifier(s):
OSTI ID: 1463748
Report Number(s):
Journal ID: ISSN 1477-9226
Grant/Contract Number:  
Resource Type:
Accepted Manuscript
Journal Name:
Dalton Transactions
Additional Journal Information:
Journal Volume: 47; Journal Issue: 35; Journal ID: ISSN 1477-9226
Royal Society of Chemistry
Country of Publication:
United States

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.
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.
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}

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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

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

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

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

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

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

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

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

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

Acylzirconocene Chloride as an “Unmasked” Acyl Anion
journal, July 1998

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

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

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

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

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

COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient
journal, January 1993

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

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

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

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

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

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 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

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

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

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 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

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

Rapid and ordered carbonylation and oxygenation of a cobalt( ii ) methyl
journal, January 2017

  • Reinig, Regina R.; Fought, Ellie L.; Ellern, Arkady
  • Chemical Communications, Vol. 53, Issue 80
  • DOI: 10.1039/C7CC06339C

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

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

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

Metals and Their Scaffolds to Promote Difficult Enzymatic Reactions
journal, November 2006

Taking a snapshot of the triplet excited state of an OLED organometallic luminophore using X-rays
journal, May 2020

  • Smolentsev, Grigory; Milne, Christopher J.; Guda, Alexander
  • Nature Communications, Vol. 11, Issue 1
  • DOI: 10.1038/s41467-020-15998-z