Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds

doi:10.1039/C9SC04305E

Title: Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds

Abstract

Mechanistic studies provide valuable insights into Cu-catalyzed N–N coupling reactions relevant to energy conversion and pharmaceutical synthesis.

Authors:

^[1];

^[1]; Gerken, James B. ^[1];

^[1];

^[1]; Martinelli, Joseph R. ^[2];

^[1]

Department of Chemistry, University of Wisconsin–Madison, Madison, USA
Small Molecule Design and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, USA

Publication Date:: 2020-01-01

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

OSTI Identifier:: 1579758

Grant/Contract Number:: FG02-05ER15690

Resource Type:: Published Article

Journal Name:: Chemical Science

Additional Journal Information:: Journal Name: Chemical Science; Journal ID: ISSN 2041-6520

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Ryan, Michael C., Kim, Yeon Jung, Gerken, James B., Wang, Fei, Aristov, Michael M., Martinelli, Joseph R., and Stahl, Shannon S. Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds.  United Kingdom: N. p., 2020. 
        Web.  doi:10.1039/C9SC04305E.

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                    Ryan, Michael C., Kim, Yeon Jung, Gerken, James B., Wang, Fei, Aristov, Michael M., Martinelli, Joseph R., & Stahl, Shannon S. Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds.  United Kingdom.  doi:10.1039/C9SC04305E.

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                    Ryan, Michael C., Kim, Yeon Jung, Gerken, James B., Wang, Fei, Aristov, Michael M., Martinelli, Joseph R., and Stahl, Shannon S. Wed .  
        "Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds".  United Kingdom.  doi:10.1039/C9SC04305E.

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@article{osti_1579758,

  title        = {Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds},

  author       = {Ryan, Michael C. and Kim, Yeon Jung and Gerken, James B. and Wang, Fei and Aristov, Michael M. and Martinelli, Joseph R. and Stahl, Shannon S.},

  abstractNote = {Mechanistic studies provide valuable insights into Cu-catalyzed N–N coupling reactions relevant to energy conversion and pharmaceutical synthesis.},

  doi          = {10.1039/C9SC04305E},

  journal      = {Chemical Science},

  number       = ,

  volume       = ,

  place        = {United Kingdom},

  year         = {2020},

  month        = {1}

}

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DOI: 10.1039/C9SC04305E

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Title: Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds

Abstract

Citation Formats

journal, January 2012

Copper(II) Anilides in sp 3 C-H Amination journal, July 2014

Access to Pyrazolidin-3,5-diones through Anodic N-N Bond Formation journal, July 2016

Copper-Catalyzed Synthesis of Imidazo[1,2- a ]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale journal, June 2013

Gold-Catalyzed Synthesis of Aromatic Azo Compounds from Anilines and Nitroaromatics journal, December 2008

Insights into the Mechanism of Anodic N–N Bond Formation by Dehydrogenative Coupling journal, August 2017

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

Hydrazine Production from Ammonia via Azine journal, December 1976

Copper-catalyzed oxidative coupling of diphenylmethanimine promoted by some monodentate pyridines*1 journal, March 1976

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling journal, June 2018

Hydrazine Synthesis by a Catalytic Oxidation Process journal, August 1990

Reactivity of Dioxygen−Copper Systems journal, February 2004

Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst journal, May 2015

“Dimerization” of Organic Nitrogen Compoundsvia Copper-Containing Intermediates journal, July 1967

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Mechanistic Study of Copper-Catalyzed Aerobic Oxidative Coupling of Arylboronic Esters and Methanol: Insights into an Organometallic Oxidase Reaction journal, April 2009

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Structure and Spectroscopy of Copper−Dioxygen Complexes journal, February 2004

Rh III /Cu II -Cocatalyzed Synthesis of 1 H -Indazoles through C–H Amidation and N–N Bond Formation journal, June 2013

Copper-Catalyzed Aerobic Oxidative CH Functionalizations: Trends and Mechanistic Insights journal, October 2011

Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems journal, July 2014

Total Synthesis of Dixiamycin B by Electrochemical Oxidation journal, April 2014

Facile Synthesis of 1,2,4-Triazoles via a Copper-Catalyzed Tandem Addition−Oxidative Cyclization journal, October 2009

Copper-Catalyzed Oxidative Alkynylation of Diaryl Imines with Terminal Alkynes: A Facile Synthesis of Ynimines journal, December 2011

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Electrolysis of liquid ammonia for hydrogen generation journal, January 2015

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Elusive Terminal Copper Arylnitrene Intermediates journal, May 2017

Recent Advances in Nitrogen–Nitrogen Bond Formation journal, August 2017

Copper(II) Anilides in sp ³ C-H Amination
journal, July 2014

Access to Pyrazolidin-3,5-diones through Anodic N-N Bond Formation
journal, July 2016

Copper-Catalyzed Synthesis of Imidazo[1,2- a ]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale
journal, June 2013

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Insights into the Mechanism of Anodic N–N Bond Formation by Dehydrogenative Coupling
journal, August 2017

Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen-Coupled Turnover
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Hydrazine Production from Ammonia via Azine
journal, December 1976

Copper-catalyzed oxidative coupling of diphenylmethanimine promoted by some monodentate pyridines*1
journal, March 1976

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling
journal, June 2018

Hydrazine Synthesis by a Catalytic Oxidation Process
journal, August 1990

Reactivity of Dioxygen−Copper Systems
journal, February 2004

Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst
journal, May 2015

“Dimerization” of Organic Nitrogen Compoundsvia Copper-Containing Intermediates
journal, July 1967

Mild Cu(OAc) ₂ ·H ₂ O-catalyzed synthesis of multi-substituted 1,2,4-triazoles from amidines with nitriles via a N–N/C–N coupling
journal, January 2015

Effects of Electron-Deficient β-Diketiminate and Formazan Supporting Ligands on Copper(I)-Mediated Dioxygen Activation
journal, May 2009

Synthesis of azobenzenes: the coloured pieces of molecular materials
journal, January 2011

A Synthesis of 1 H -Indazoles via a Cu(OAc) ₂ -Catalyzed N–N Bond Formation
journal, March 2016

Benzophenoneimine Complexes of Copper(1)
journal, July 1997

Metal Complexes of Aminyl Radicals
journal, September 2008

1,3,5-Triazapentadienes as Chelating Ligands: 1,2,4-Triphenyl-1,3,5-triaza-pentadiene Complexes of Cobalt(II), Nickel(II), Palladium(II), Copper(II) and Zinc(II)
journal, June 2005

Mechanistic Study of Copper-Catalyzed Aerobic Oxidative Coupling of Arylboronic Esters and Methanol: Insights into an Organometallic Oxidase Reaction
journal, April 2009

Electrochemical Conversion of Phthaldianilides to Phthalazin-1,4-diones by Dehydrogenative N−N Bond Formation
journal, December 2017

Natural Products Containing a Nitrogen–Nitrogen Bond
journal, March 2013

Dioxygen Activation at a Single Copper Site: Structure, Bonding, and Mechanism of Formation of 1:1 Cu−O ₂ Adducts
journal, December 2004

Structure and Spectroscopy of Copper−Dioxygen Complexes
journal, February 2004

Rh ^III /Cu ^II -Cocatalyzed Synthesis of 1 H -Indazoles through C–H Amidation and N–N Bond Formation
journal, June 2013

Copper-Catalyzed Aerobic Oxidative CH Functionalizations: Trends and Mechanistic Insights
journal, October 2011

Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems
journal, July 2014

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journal, April 2014

Facile Synthesis of 1,2,4-Triazoles via a Copper-Catalyzed Tandem Addition−Oxidative Cyclization
journal, October 2009

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journal, December 2011

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journal, September 2010

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journal, January 2015

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