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

Title: Ni(bpy)(cod)-Catalyzed Hydroboration of Ketones, Aldehydes, and Imines: Observation of Redox Changes Within the Bipyridine Ligand

Authors:
; ; ; ; ; ; ;
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE Laboratory Directed Research and Development (LDRD) Program
OSTI Identifier:
1495127
Report Number(s):
LA-UR-15-27855
Journal ID: ISSN 1434-1948
DOE Contract Number:  
89233218CNA000001
Resource Type:
Journal Article
Journal Name:
European Journal of Inorganic Chemistry
Additional Journal Information:
Journal Volume: 2016; Journal Issue: 11; Journal ID: ISSN 1434-1948
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
Inorganic and Physical Chemistry; Organic Chemistry

Citation Formats

King, Amanda E., Stieber, S. Chantal E., Henson, Neil J., Kozimor, Stosh A., Scott, Brian L., Smythe, Nathan C., Sutton, Andrew D., and Gordon, John C. Ni(bpy)(cod)-Catalyzed Hydroboration of Ketones, Aldehydes, and Imines: Observation of Redox Changes Within the Bipyridine Ligand. United States: N. p., 2016. Web. doi:10.1002/ejic.201600143.
King, Amanda E., Stieber, S. Chantal E., Henson, Neil J., Kozimor, Stosh A., Scott, Brian L., Smythe, Nathan C., Sutton, Andrew D., & Gordon, John C. Ni(bpy)(cod)-Catalyzed Hydroboration of Ketones, Aldehydes, and Imines: Observation of Redox Changes Within the Bipyridine Ligand. United States. doi:10.1002/ejic.201600143.
King, Amanda E., Stieber, S. Chantal E., Henson, Neil J., Kozimor, Stosh A., Scott, Brian L., Smythe, Nathan C., Sutton, Andrew D., and Gordon, John C. Fri . "Ni(bpy)(cod)-Catalyzed Hydroboration of Ketones, Aldehydes, and Imines: Observation of Redox Changes Within the Bipyridine Ligand". United States. doi:10.1002/ejic.201600143.
@article{osti_1495127,
title = {Ni(bpy)(cod)-Catalyzed Hydroboration of Ketones, Aldehydes, and Imines: Observation of Redox Changes Within the Bipyridine Ligand},
author = {King, Amanda E. and Stieber, S. Chantal E. and Henson, Neil J. and Kozimor, Stosh A. and Scott, Brian L. and Smythe, Nathan C. and Sutton, Andrew D. and Gordon, John C.},
abstractNote = {},
doi = {10.1002/ejic.201600143},
journal = {European Journal of Inorganic Chemistry},
issn = {1434-1948},
number = 11,
volume = 2016,
place = {United States},
year = {2016},
month = {3}
}

Works referenced in this record:

Low-Valent α-Diimine Iron Complexes for Catalytic Olefin Hydrogenation
journal, November 2005

  • Bart, Suzanne C.; Hawrelak, Eric J.; Lobkovsky, Emil
  • Organometallics, Vol. 24, Issue 23
  • DOI: 10.1021/om050625b

Alkane dehydrogenation by iridium complexes
journal, January 1982

  • Crabtree, Robert H.; Mellea, Michelle F.; Mihelcic, Jean M.
  • Journal of the American Chemical Society, Vol. 104, Issue 1
  • DOI: 10.1021/ja00365a021

Stereochimie du motif de coordination dans les complexes a ligands mixtes du type MII(bipy)(H2O)2AB4 (MII = NiII ou CuII; AB42− = SO42− ou BeF42−) bipy: 2,2′ bipyridine
journal, January 1976

  • Tedenac, J. C.; Phung, Nguyen Dinh; Avinens, C.
  • Journal of Inorganic and Nuclear Chemistry, Vol. 38, Issue 1
  • DOI: 10.1016/0022-1902(76)80055-3

Functional Group Tolerance and Substrate Scope in Bis(imino)pyridine Iron Catalyzed Alkene Hydrogenation
journal, April 2008

  • Trovitch, Ryan J.; Lobkovsky, Emil; Bill, Eckhard
  • Organometallics, Vol. 27, Issue 7, p. 1470-1478
  • DOI: 10.1021/om701091z

Dibenzo[a,e]cyclooctatetraene in a proposed test for heterogeneity in catalysts formed from soluble platinum-group metal complexes
journal, July 1983

  • Anton, Douglas R.; Crabtree, Robert H.
  • Organometallics, Vol. 2, Issue 7
  • DOI: 10.1021/om50001a013

Understanding Ketone Hydrodeoxygenation for the Production of Fuels and Feedstocks From Biomass
journal, January 2015

  • King, Amanda E.; Brooks, Ty J.; Tian, Yong-Hui
  • ACS Catalysis, Vol. 5, Issue 2
  • DOI: 10.1021/cs501965w

Catalytic proton reduction with transition metal complexes of the redox-active ligand bpy2PYMe
journal, January 2013

  • Nippe, Michael; Khnayzer, Rony S.; Panetier, Julien A.
  • Chemical Science, Vol. 4, Issue 10
  • DOI: 10.1039/c3sc51660a

Tuning the Oxidation Level, the Spin State, and the Degree of Electron Delocalization in Homo- and Heteroleptic Bis(α-diimine)iron Complexes
journal, January 2009

  • Khusniyarov, Marat M.; Weyhermüller, Thomas; Bill, Eckhard
  • Journal of the American Chemical Society, Vol. 131, Issue 3
  • DOI: 10.1021/ja808149k

Magnesium-catalysed hydroboration of aldehydes and ketones
journal, January 2012

  • Arrowsmith, Merle; Hadlington, Terrance J.; Hill, Michael S.
  • Chemical Communications, Vol. 48, Issue 38
  • DOI: 10.1039/c2cc30565h

Magnesium Catalysis of Imine Hydroboration
journal, January 2013

  • Arrowsmith, Merle; Hill, Michael S.; Kociok-Köhn, Gabriele
  • Chemistry - A European Journal, Vol. 19, Issue 8
  • DOI: 10.1002/chem.201203190

Combination of Redox-Active Ligand and Lewis Acid for Dioxygen Reduction with π-Bound Molybdenum−Quinonoid Complexes
journal, January 2015

  • Henthorn, Justin T.; Lin, Sibo; Agapie, Theodor
  • Journal of the American Chemical Society, Vol. 137, Issue 4
  • DOI: 10.1021/ja5100405

Transition-Metal Complexes with Singly Reduced 1,2-Diketone Radical Ligands
journal, April 2008

  • Spikes, Geoffrey H.; Bill, Eckhard; Weyhermüller, Thomas
  • Angewandte Chemie International Edition, Vol. 47, Issue 16
  • DOI: 10.1002/anie.200705410

Nickelacyclopentene Derivatives from Nickel(0), Carbon Monoxide and Alkyne
journal, November 1980

  • Hoberg, Heinz; Herrera, Antonio
  • Angewandte Chemie International Edition in English, Vol. 19, Issue 11
  • DOI: 10.1002/anie.198009271

Selective hydrogenation of the C=O bond of ketones using Ni(0) complexes with a chelating bisphosphine
journal, August 2009

  • Flores-Gaspar, Areli; Pinedo-González, Paulina; Crestani, Marco G.
  • Journal of Molecular Catalysis A: Chemical, Vol. 309, Issue 1-2, p. 1-11
  • DOI: 10.1016/j.molcata.2009.05.026

2,2′-dipyridyl-1,5-cyclooctadiennickel(0): kristall-und molekülstruktur
journal, September 1982


Experimental Electron Density Studies for Investigating the Metal π-Ligand Bond:  the Case of Bis(1,5-cyclooctadiene)nickel
journal, February 1998

  • Macchi, Piero; Proserpio, Davide M.; Sironi, Angelo
  • Journal of the American Chemical Society, Vol. 120, Issue 7
  • DOI: 10.1021/ja972558l

Iron Dicarbonyl Complexes Featuring Bipyridine-Based PNN Pincer Ligands with Short Interpyridine CC Bond Lengths: Innocent or Non-Innocent Ligand?
journal, March 2014

  • Zell, Thomas; Milko, Petr; Fillman, Kathlyn L.
  • Chemistry - A European Journal, Vol. 20, Issue 15
  • DOI: 10.1002/chem.201304631

Catalytic Hydroboration of Carbonyl Derivatives, Imines, and Carbon Dioxide
journal, April 2015


Metal-Free σ-Bond Metathesis in 1,3,2-Diazaphospholene-Catalyzed Hydroboration of Carbonyl Compounds
journal, November 2014

  • Chong, Che Chang; Hirao, Hajime; Kinjo, Rei
  • Angewandte Chemie International Edition, Vol. 54, Issue 1
  • DOI: 10.1002/anie.201408760

The hydrodeoxygenation of bioderived furans into alkanes
journal, April 2013

  • Sutton, Andrew D.; Waldie, Fraser D.; Wu, Ruilian
  • Nature Chemistry, Vol. 5, Issue 5, p. 428-432
  • DOI: 10.1038/nchem.1609

Access to formally Ni( i ) states in a heterobimetallic NiZn system
journal, January 2013

  • Uyeda, Christopher; Peters, Jonas C.
  • Chem. Sci., Vol. 4, Issue 1
  • DOI: 10.1039/C2SC21231E

Reactions of Aldehydes with Carbon Dioxide at Nickel(0) Centers. A Detailed Kinetic Analysis
journal, January 1998

  • Geyer, Christian; Dinjus, Eckhard; Schindler, Siegfried
  • Organometallics, Vol. 17, Issue 1
  • DOI: 10.1021/om970584m

A Redox-Active Ligand as a Reservoir for Protons and Electrons: O2 Reduction at Zirconium(IV)
journal, October 2011

  • Lu, Feng; Zarkesh, Ryan A.; Heyduk, Alan F.
  • European Journal of Inorganic Chemistry, Vol. 2012, Issue 3
  • DOI: 10.1002/ejic.201100798

Catalytic Reactivity of a Zirconium(IV) Redox-Active Ligand Complex with 1,2-Diphenylhydrazine
journal, March 2008

  • Blackmore, Karen J.; Lal, Neetu; Ziller, Joseph W.
  • Journal of the American Chemical Society, Vol. 130, Issue 9
  • DOI: 10.1021/ja710611v

High-Activity Iron Catalysts for the Hydrogenation of Hindered, Unfunctionalized Alkenes
journal, July 2012

  • Yu, Renyuan Pony; Darmon, Jonathan M.; Hoyt, Jordan M.
  • ACS Catalysis, Vol. 2, Issue 8
  • DOI: 10.1021/cs300358m

Coordination of 2,2‘-Bipyridyl and 1,10-Phenanthroline to Substituted Ytterbocenes:  An Experimental Investigation of Spin Coupling in Lanthanide Complexes
journal, February 2002

  • Schultz, Madeleine; Boncella, James M.; Berg, David J.
  • Organometallics, Vol. 21, Issue 3
  • DOI: 10.1021/om010661k

Bis(α-diimine)iron Complexes: Electronic Structure Determination by Spectroscopy and Broken Symmetry Density Functional Theoretical Calculations
journal, June 2008

  • Muresan, Nicoleta; Lu, Connie C.; Ghosh, Meenakshi
  • Inorganic Chemistry, Vol. 47, Issue 11
  • DOI: 10.1021/ic7022693

The Development of Enantioselective Rhodium-Catalysed Hydroboration of Olefins
journal, April 2005

  • Carroll, Anne-Marie; O'Sullivan, Timothy?P.; Guiry, Patrick?J.
  • Advanced Synthesis & Catalysis, Vol. 347, Issue 5
  • DOI: 10.1002/adsc.200404232

Neutral Bis(α-iminopyridine)metal Complexes of the First-Row Transition Ions (Cr, Mn, Fe, Co, Ni, Zn) and Their Monocationic Analogues:  Mixed Valency Involving a Redox Noninnocent Ligand System
journal, March 2008

  • Lu, Connie C.; Bill, Eckhard; Weyhermüller, Thomas
  • Journal of the American Chemical Society, Vol. 130, Issue 10
  • DOI: 10.1021/ja710663n

Enantioselective Reduction of Prochiral Ketones by Catecholborane Catalysed by Chiral Group 13 Complexes
journal, October 2000


Bis(2,2'-bipyridyl)diisopropoxymolybdenum(II). Structural and spectroscopic evidence for molybdenum-to-bipyridyl .pi.* bonding
journal, August 1981

  • Chisholm, M. H.; Huffman, J. C.; Rothwell, I. P.
  • Journal of the American Chemical Society, Vol. 103, Issue 16
  • DOI: 10.1021/ja00406a048

The Construction and Interpretation of Mcscf Wavefunctions
journal, October 1998


Redox-Active Ligands Facilitate Bimetallic O 2 Homolysis at Five-Coordinate Oxorhenium(V) Centers
journal, March 2010

  • Lippert, Cameron A.; Arnstein, Stephen A.; Sherrill, C. David
  • Journal of the American Chemical Society, Vol. 132, Issue 11
  • DOI: 10.1021/ja910500a

Redox-active ligand-mediated Co–Cl bond-forming reactions at reducing square planar cobalt(III) centers
journal, January 2010


On the Innocence of Bipyridine Ligands: How Well Do DFT Functionals Fare for These Challenging Spin Systems?
journal, November 2013

  • Milko, Petr; Iron, Mark A.
  • Journal of Chemical Theory and Computation, Vol. 10, Issue 1
  • DOI: 10.1021/ct400913z

Interactions of Aziridines with Nickel Complexes:  Oxidative-Addition and Reductive-Elimination Reactions that Break and Make C−N Bonds
journal, March 2002

  • Lin, Beatrice L.; Clough, Christopher R.; Hillhouse, Gregory L.
  • Journal of the American Chemical Society, Vol. 124, Issue 12
  • DOI: 10.1021/ja017652n

Hidden Noninnocence: Theoretical and Experimental Evidence for Redox Activity of a β-Diketiminate(1−) Ligand
journal, January 2011

  • Khusniyarov , Marat M.; Bill, Eckhard; Weyhermüller, Thomas
  • Angewandte Chemie International Edition, Vol. 50, Issue 7
  • DOI: 10.1002/anie.201005953

Redox-active ligands in catalysis
journal, January 2013

  • Luca, Oana R.; Crabtree, Robert H.
  • Chem. Soc. Rev., Vol. 42, Issue 4
  • DOI: 10.1039/C2CS35228A

Synthesis of Electron-Rich Uranium(IV) Complexes Supported by Tridentate Schiff Base Ligands and Their Multi-Electron Redox Chemistry
journal, June 2013

  • Camp, Clément; Andrez, Julie; Pécaut, Jacques
  • Inorganic Chemistry, Vol. 52, Issue 12
  • DOI: 10.1021/ic4006218

Zur katalytischen Dimerisierung von Propionaldehyd druch Gemischt-Ligand-Nickel(O)-Komplexe
journal, May 1978

  • Walther, D.; Dinjus, E.
  • Zeitschrift f�r anorganische und allgemeine Chemie, Vol. 440, Issue 1
  • DOI: 10.1002/zaac.19784400102

Redox Non-Innocent Ligands: Versatile New Tools to Control Catalytic Reactions
journal, January 2012

  • Lyaskovskyy, Volodymyr; de Bruin, Bas
  • ACS Catalysis, Vol. 2, Issue 2
  • DOI: 10.1021/cs200660v

.pi. Complexes of nickel(0) and ketones. Mechanism of formation and the crystal structure of (benzophenone)bis(triethylphosphine)nickel
journal, August 1979

  • Tsou, T. T.; Huffman, J. C.; Kochi, J. K.
  • Inorganic Chemistry, Vol. 18, Issue 8
  • DOI: 10.1021/ic50198a054

Selective Substituent Transfer from Mixed Zinc Reagents in Ni-Catalyzed Anhydride Alkylation
journal, September 2006

  • Johnson, Jeffrey B.; Yu, Robert T.; Fink, Paul
  • Organic Letters, Vol. 8, Issue 19
  • DOI: 10.1021/ol0616337

Amino Acid Derived Nickelacycles:  Intermediates in Nickel-Mediated Polypeptide Synthesis
journal, May 1998

  • Deming, Timothy J.
  • Journal of the American Chemical Society, Vol. 120, Issue 17
  • DOI: 10.1021/ja980313i

Kinetic Analysis of the Reaction of Isoprene with Carbon Dioxide and a Nickel(0) Complex
journal, September 1998

  • Geyer, Christian; Schindler, Siegfried
  • Organometallics, Vol. 17, Issue 20
  • DOI: 10.1021/om980275b

An Intermediate and Its Secondary Products in a Nickel-Catalyzed Synthesis of [4]-Radialenes
journal, June 1985

  • Stehling, Ludwig; Wilke, G�nther
  • Angewandte Chemie International Edition in English, Vol. 24, Issue 6
  • DOI: 10.1002/anie.198504961

Low Coordinate Germanium(II) and Tin(II) Hydride Complexes: Efficient Catalysts for the Hydroboration of Carbonyl Compounds
journal, February 2014

  • Hadlington, Terrance J.; Hermann, Markus; Frenking, Gernot
  • Journal of the American Chemical Society, Vol. 136, Issue 8
  • DOI: 10.1021/ja5006477

Coinage metal-catalyzed hydroboration of imines
journal, August 1995

  • Baker, R. Thomas; Calabrese, Joseph C.; Westcott, Stephen A.
  • Journal of Organometallic Chemistry, Vol. 498, Issue 2
  • DOI: 10.1016/0022-328X(95)05499-F

Nickelacyclopentane derivatives as intermediates in the nickel(0)-catalysed cyclodimerisation of strained-ring olefins
journal, January 1976

  • Doyle, Michael J.; McMeeking, John; Binger, Paul
  • Journal of the Chemical Society, Chemical Communications, Issue 11
  • DOI: 10.1039/c39760000376

A Boron-Substituted Analogue of the Shvo Hydrogenation Catalyst: Catalytic Hydroboration of Aldehydes, Imines, and Ketones
journal, April 2009

  • Koren-Selfridge, Liza; Londino, Hannah N.; Vellucci, Jessica K.
  • Organometallics, Vol. 28, Issue 7
  • DOI: 10.1021/om801228m

Synthesis and Characterization of Alkali-Metal Salts of 2,2′- and 2,4′-Bipyridyl Radicals and Dianions
journal, September 2009

  • Gore-Randall, Edward; Irwin, Mark; Denning, Mark S.
  • Inorganic Chemistry, Vol. 48, Issue 17
  • DOI: 10.1021/ic9009459

Catalytic hydroboration by an imido-hydrido complex of Mo( iv )
journal, January 2012

  • Khalimon, Andrey Y.; Farha, Philip; Kuzmina, Lyudmila G.
  • Chem. Commun., Vol. 48, Issue 3
  • DOI: 10.1039/C1CC14508H

The Monoanionic π-Radical Redox State of α-Iminoketones in Bis(ligand)metal Complexes of Nickel and Cobalt
journal, September 2007

  • Lu, Connie C.; Bill, Eckhard; Weyhermüller, Thomas
  • Inorganic Chemistry, Vol. 46, Issue 19
  • DOI: 10.1021/ic7008094

Redox-Active Ligand-Mediated Oxidative Addition and Reductive Elimination at Square Planar Cobalt(III): Multielectron Reactions for Cross-Coupling
journal, October 2010

  • Smith, Aubrey L.; Hardcastle, Kenneth I.; Soper, Jake D.
  • Journal of the American Chemical Society, Vol. 132, Issue 41
  • DOI: 10.1021/ja106212w

Electrocatalytic Hydrogen Production by an Aluminum(III) Complex: Ligand-Based Proton and Electron Transfer
journal, August 2015

  • Thompson, Emily J.; Berben, Louise A.
  • Angewandte Chemie International Edition, Vol. 54, Issue 40
  • DOI: 10.1002/anie.201503935

Titanocene(II)-Catalyzed Hydroboration of Carbonyl Compounds
journal, December 2012

  • Oluyadi, Abdulafeez A.; Ma, Shuhua; Muhoro, Clare N.
  • Organometallics, Vol. 32, Issue 1
  • DOI: 10.1021/om300828m

Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds
journal, September 2015


Catalytic Hydrogenation Activity and Electronic Structure Determination of Bis(arylimidazol-2-ylidene)pyridine Cobalt Alkyl and Hydride Complexes
journal, August 2013

  • Yu, Renyuan Pony; Darmon, Jonathan M.; Milsmann, Carsten
  • Journal of the American Chemical Society, Vol. 135, Issue 35
  • DOI: 10.1021/ja406608u

Enantiopure C1-Symmetric Bis(imino)pyridine Cobalt Complexes for Asymmetric Alkene Hydrogenation
journal, March 2012

  • Monfette, Sebastien; Turner, Zoë R.; Semproni, Scott P.
  • Journal of the American Chemical Society, Vol. 134, Issue 10, p. 4561-4564
  • DOI: 10.1021/ja300503k

Bipyridine Radical Ions
journal, April 1982


Radical anionic versus neutral 2,2′-bipyridyl coordination in uranium complexes supported by amide and ketimide ligands
journal, January 2015

  • Diaconescu, Paula L.; Cummins, Christopher C.
  • Dalton Transactions, Vol. 44, Issue 6
  • DOI: 10.1039/C4DT02422B

Catalytic nitrene transfer by a zirconium( iv ) redox-active ligand complex
journal, January 2011

  • Nguyen, Andy I.; Zarkesh, Ryan A.; Lacy, David C.
  • Chem. Sci., Vol. 2, Issue 1
  • DOI: 10.1039/C0SC00414F

Designing Catalysts for Nitrene Transfer Using Early Transition Metals and Redox-Active Ligands
journal, October 2011

  • Heyduk, Alan F.; Zarkesh, Ryan A.; Nguyen, Andy I.
  • Inorganic Chemistry, Vol. 50, Issue 20
  • DOI: 10.1021/ic200911b

Development of an Efficient Photocatalytic System for CO 2 Reduction Using Rhenium(I) Complexes Based on Mechanistic Studies
journal, February 2008

  • Takeda, Hiroyuki; Koike, Kazuhide; Inoue, Haruo
  • Journal of the American Chemical Society, Vol. 130, Issue 6
  • DOI: 10.1021/ja077752e

Charge-shift bonding and its manifestations in chemistry
journal, August 2009

  • Shaik, Sason; Danovich, David; Wu, Wei
  • Nature Chemistry, Vol. 1, Issue 6
  • DOI: 10.1038/nchem.327

An Aluminum Hydride That Functions like a Transition-Metal Catalyst
journal, June 2015

  • Yang, Zhi; Zhong, Mingdong; Ma, Xiaoli
  • Angewandte Chemie International Edition, Vol. 54, Issue 35
  • DOI: 10.1002/anie.201503304

Zur oxydativen Addition von Benzylhalogeniden an Nickel(O)-Komplexe
journal, August 1975

  • Bartsch, Ekkehard; Dinjus, Eckhard; Uhlig, Egon
  • Zeitschrift für Chemie, Vol. 15, Issue 8
  • DOI: 10.1002/zfch.19750150820

Spectro-electrochemical studies on tris-bipyridyl ruthenium complexes; ultra-violet, visible, and near-infrared spectra of the series [Ru(bipyridyl)3]2+/1+/0/1?
journal, January 1981

  • Heath, Graham A.; Yellowlees, Lesley J.; Braterman, Paul S.
  • Journal of the Chemical Society, Chemical Communications, Issue 6
  • DOI: 10.1039/c39810000287

Iron-Catalyzed, Hydrogen-Mediated Reductive Cyclization of 1,6-Enynes and Diynes: Evidence for Bis(imino)pyridine Ligand Participation
journal, July 2009

  • Sylvester, Kevin T.; Chirik, Paul J.
  • Journal of the American Chemical Society, Vol. 131, Issue 25
  • DOI: 10.1021/ja902478p

Radical Ligands Confer Nobility on Base-Metal Catalysts
journal, February 2010


How Innocent are Potentially Redox Non-Innocent Ligands? Electronic Structure and Metal Oxidation States in Iron-PNN Complexes as a Representative Case Study
journal, April 2015


Iron- and Cobalt-Catalyzed Alkene Hydrogenation: Catalysis with Both Redox-Active and Strong Field Ligands
journal, May 2015