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:: 2020-01-29

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

OSTI Identifier:: 1579758

Grant/Contract Number:: FG02-05ER15690

Resource Type:: Published Article

Journal Name:: Chemical Science

Additional Journal Information:: Journal Name: Chemical Science Journal Volume: 11 Journal Issue: 4; 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.

Copy to clipboard


                    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.

Copy to clipboard


                    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.

Copy to clipboard


                    
@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       = 4,

  volume       = 11,

  place        = {United Kingdom},

  year         = {2020},

  month        = {1}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Publisher's Version of Record
DOI: 10.1039/C9SC04305E

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 3 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

Recent Researches in Triazole Compounds as Medicinal Drugs
journal, January 2012

-H. Zhou, C.; Wang, Y.
Current Medicinal Chemistry, Vol. 19, Issue 2
DOI: 10.2174/092986712803414213

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

Jang, Eun Sil; McMullin, Claire L.; Käß, Martina
Journal of the American Chemical Society, Vol. 136, Issue 31
DOI: 10.1021/ja5026547

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

Gieshoff, Tile; Schollmeyer, Dieter; Waldvogel, Siegfried R.
Angewandte Chemie International Edition, Vol. 55, Issue 32
DOI: 10.1002/anie.201603899

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

Bagdi, Avik Kumar; Rahman, Matiur; Santra, Sougata
Advanced Synthesis & Catalysis, Vol. 355, Issue 9
DOI: 10.1002/adsc.201300298

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

Grirrane, A.; Corma, A.; Garcia, H.
Science, Vol. 322, Issue 5908
DOI: 10.1126/science.1166401

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

Gieshoff, Tile; Kehl, Anton; Schollmeyer, Dieter
Journal of the American Chemical Society, Vol. 139, Issue 35
DOI: 10.1021/jacs.7b07488

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

Stahl, Shannon S.
Angewandte Chemie International Edition, Vol. 43, Issue 26
DOI: 10.1002/anie.200300630

Hydrazine Production from Ammonia via Azine
journal, December 1976

Hayashi, Hiromu; Kainoh, Akihiko; Katayama, Masayoshi
Industrial & Engineering Chemistry Product Research and Development, Vol. 15, Issue 4
DOI: 10.1021/i360060a016

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

Hayashi, H.
Journal of Catalysis, Vol. 41, Issue 3
DOI: 10.1016/0021-9517(76)90237-2

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

Ryan, Michael C.; Martinelli, Joseph R.; Stahl, Shannon S.
Journal of the American Chemical Society, Vol. 140, Issue 29
DOI: 10.1021/jacs.8b05245

Hydrazine Synthesis by a Catalytic Oxidation Process
journal, August 1990

Hayashi, Hiromu
Catalysis Reviews, Vol. 32, Issue 3
DOI: 10.1080/01614949009351352

Reactivity of Dioxygen−Copper Systems
journal, February 2004

Lewis, Elizabeth A.; Tolman, William B.
Chemical Reviews, Vol. 104, Issue 2
DOI: 10.1021/cr020633r

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

McCann, Scott D.; Stahl, Shannon S.
Accounts of Chemical Research, Vol. 48, Issue 6
DOI: 10.1021/acs.accounts.5b00060

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

Kauffmann, Th.; Albrecht, J.; Berger, D.
Angewandte Chemie International Edition in English, Vol. 6, Issue 7
DOI: 10.1002/anie.196706331

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

Wang, Fei; You, Qing; Wu, Chaoting
RSC Advances, Vol. 5, Issue 96
DOI: 10.1039/C5RA15919A

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

Hong, Sungjun; Hill, Lyndal M. R.; Gupta, Aalo K.
Inorganic Chemistry, Vol. 48, Issue 10
DOI: 10.1021/ic9002466

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

Merino, Estíbaliz
Chemical Society Reviews, Vol. 40, Issue 7
DOI: 10.1039/c0cs00183j

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

Chen, Cheng-yi; Tang, Guangrong; He, Fengxian
Organic Letters, Vol. 18, Issue 7
DOI: 10.1021/acs.orglett.6b00611

Benzophenoneimine Complexes of Copper(1)
journal, July 1997

Schneider, Wolfgang; Bauer, Andreas; Schmidbaur, Hubert
Chemische Berichte, Vol. 130, Issue 7
DOI: 10.1002/cber.19971300721

Metal Complexes of Aminyl Radicals
journal, September 2008

Hicks, Robin G.
Angewandte Chemie International Edition, Vol. 47, Issue 39
DOI: 10.1002/anie.200802713

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

Heße, Nadine; Fröhlich, Roland; Humelnicu, Ionel
European Journal of Inorganic Chemistry, Vol. 2005, Issue 11
DOI: 10.1002/ejic.200401010

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

King, Amanda E.; Brunold, Thomas C.; Stahl, Shannon S.
Journal of the American Chemical Society, Vol. 131, Issue 14
DOI: 10.1021/ja9006657

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

Kehl, Anton; Gieshoff, Tile; Schollmeyer, Dieter
Chemistry - A European Journal, Vol. 24, Issue 3
DOI: 10.1002/chem.201705578

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

Blair, Lachlan M.; Sperry, Jonathan
Journal of Natural Products, Vol. 76, Issue 4
DOI: 10.1021/np400124n

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

Aboelella, Nermeen W.; Kryatov, Sergey V.; Gherman, Benjamin F.
Journal of the American Chemical Society, Vol. 126, Issue 51
DOI: 10.1021/ja045678j

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

Mirica, Liviu M.; Ottenwaelder, Xavier; Stack, T. Daniel P.
Chemical Reviews, Vol. 104, Issue 2
DOI: 10.1021/cr020632z

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

Yu, Da-Gang; Suri, Mamta; Glorius, Frank
Journal of the American Chemical Society, Vol. 135, Issue 24
DOI: 10.1021/ja4033555

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

Wendlandt, Alison E.; Suess, Alison M.; Stahl, Shannon S.
Angewandte Chemie International Edition, Vol. 50, Issue 47
DOI: 10.1002/anie.201103945

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

Ryland, Bradford L.; Stahl, Shannon S.
Angewandte Chemie International Edition, Vol. 53, Issue 34
DOI: 10.1002/anie.201403110

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

Rosen, Brandon R.; Werner, Erik W.; O’Brien, Alexander G.
Journal of the American Chemical Society, Vol. 136, Issue 15
DOI: 10.1021/ja5013323

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

Ueda, Satoshi; Nagasawa, Hideko
Journal of the American Chemical Society, Vol. 131, Issue 42
DOI: 10.1021/ja905056z

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

Laouiti, Anouar; Rammah, Mohamed M.; Rammah, Mohamed B.
Organic Letters, Vol. 14, Issue 1
DOI: 10.1021/ol2032152

A Direct Intramolecular C−H Amination Reaction Cocatalyzed by Copper(II) and Iron(III) as Part of an Efficient Route for the Synthesis of Pyrido[1,2- a ]benzimidazoles from N -Aryl-2-aminopyridines
journal, September 2010

Wang, Honggen; Wang, Yong; Peng, Changlan
Journal of the American Chemical Society, Vol. 132, Issue 38
DOI: 10.1021/ja1067993

Electrolysis of liquid ammonia for hydrogen generation
journal, January 2015

Little, Daniel J.; Smith, III, Milton R.; Hamann, Thomas W.
Energy & Environmental Science, Vol. 8, Issue 9
DOI: 10.1039/C5EE01840D

Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives
journal, December 2014

Bartels, Björn; Bolas, Conor Gordon; Cueni, Philipp
The Journal of Organic Chemistry, Vol. 80, Issue 2
DOI: 10.1021/jo502536t

Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines Leading to Aromatic Azo Compounds using Dioxygen as an Oxidant
journal, July 2010

Zhang, Chun; Jiao, Ning
Angewandte Chemie International Edition, Vol. 49, Issue 35
DOI: 10.1002/anie.201001651

Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation
journal, January 2013

Hoover, Jessica M.; Ryland, Bradford L.; Stahl, Shannon S.
Journal of the American Chemical Society, Vol. 135, Issue 6
DOI: 10.1021/ja3117203

Elusive Terminal Copper Arylnitrene Intermediates
journal, May 2017

Bakhoda, Abolghasem Gus; Jiang, Quan; Bertke, Jeffery A.
Angewandte Chemie International Edition, Vol. 56, Issue 23
DOI: 10.1002/anie.201611275

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

Guo, Qihang; Lu, Zhan
Synthesis, Vol. 49, Issue 17
DOI: 10.1055/s-0036-1588512

Similar Records in DOE PAGES and OSTI.GOV collections:

Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine

Journal Article Wu, Kun ; Huang, Zhiliang ; Qi, Xiaotian ; ... - Science Advances

Copper-catalyzed aerobic oxidative C–H/N–H coupling between simple ketones and diamines was developed toward the synthesis of a variety of pyrazines. Various substituted ketones were compatible for this transformation. Preliminary mechanistic investigations indicated that radical species were involved. X-ray absorption fine structure experiments elucidated that the Cu(II) species 5 coordinated by two N atoms at a distance of 2.04 Å and two O atoms at a shorter distance of 1.98 Å was a reactive one for this aerobic oxidative coupling reaction. Density functional theory calculations suggested that the intramolecular coupling of cationic radicals was favorable in this transformation.
Cited by 16
DOI: 10.1126/sciadv.1500656

Full Text Available
Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

Journal Article Ryan, Michael C. ; Martinelli, Joseph R. ; Stahl, Shannon S. - Journal of the American Chemical Society

A Cu-catalyzed method has been identified for aerobic oxidative dimerization of carbazoles and diarylamines to the corresponding N–N coupled bicarbazoles and tetraarylhydrazines. The reactions proceed under mild conditions (1 atm O₂, 60–80 °C) with a catalyst composed of CuBr·dimethylsulfide and N,N-dimethylaminopyridine. Reactions between carbazole and diarylamines show unusually selective cross-coupling, even with a 1:1 ratio of the two substrates. This behavior was found to arise from reversible formation of the tetraarylhydrazine. Lastly, formation of this species is kinetically favored, but cleavage of the N–N bond under the reaction conditions leads to selective formation of the thermodynamically favored cross-coupling product.
Cited by 9
DOI: 10.1021/jacs.8b05245

Full Text Available
Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C-H Bond Activation

Journal Article Lewis, Jared ; Bergman, Robert ; Ellman, Jonathan - Accounts of Chemical Research

Nitrogen heterocycles are present in many compounds of enormous practical importance, ranging from pharmaceutical agents and biological probes to electroactive materials. Direct funtionalization of nitrogen heterocycles through C-H bond activation constitutes a powerful means of regioselectively introducing a variety of substituents with diverse functional groups onto the heterocycle scaffold. Working together, our two groups have developed a family of Rh-catalyzed heterocycle alkylation and arylation reactions that are notable for their high level of functional-group compatibility. This Account describes their work in this area, emphasizing the relevant mechanistic insights that enabled synthetic advances and distinguished the resulting transformations from other methods.more »« less
DOI: 10.1021/ar800042p

Full Text Available
Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules

Journal Article Hruszkewycz, Damian P. ; Miles, Kelsey C. ; Thiel, Oliver R. ; ... - Chemical Science

A simple cobalt(II)/N-hydroxyphthalimide catalyst system has been identified for selective conversion of benzylic methylene groups in pharmaceutically relevant (hetero)arenes to the corresponding (hetero)aryl ketones. The radical reaction pathway tolerates electronically diverse benzylic C–H bonds, contrasting recent oxygenation reactions that are initiated by deprotonation of a benzylic C–H bond. The reactions proceed under practical reaction conditions (1 M substrate in BuOAc or EtOAc solvent, 12 h, 90–100 °C), and they tolerate common heterocycles, such as pyridines and imidazoles. A cobalt-free, electrochemical, NHPI-catalyzed oxygenation method overcomes challenges encountered with chelating substrates that inhibit the chemical reaction. The utility of the aerobic oxidationmore »« less
Cited by 52
DOI: 10.1039/c6sc03831j

Full Text Available
Transition Metal Catalyzed Hydroarylation of Multiple Bonds: Exploration of Second Generation Ruthenium Catalysts and Extension to Copper Systems

Technical Report Gunnoe, T Brent

Catalysts provide foundational technology for the development of new materials and can enhance the efficiency of routes to known materials. New catalyst technologies offer the possibility of reducing energy and raw material consumption as well as enabling chemical processes with a lower environmental impact. The rising demand and expense of fossil resources has strained national and global economies and has increased the importance of accessing more efficient catalytic processes for the conversion of hydrocarbons to useful products. The goals of the research are to develop and understand single-site homogeneous catalysts for the conversion of readily available hydrocarbons into useful materials.more »« less
DOI: 10.2172/1005126

Full Text Available

Similar Records

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

Abstract

Citation Formats

Recent Researches in Triazole Compounds as Medicinal Drugs 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

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

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

A Direct Intramolecular C−H Amination Reaction Cocatalyzed by Copper(II) and Iron(III) as Part of an Efficient Route for the Synthesis of Pyrido[1,2- a ]benzimidazoles from N -Aryl-2-aminopyridines journal, September 2010

Electrolysis of liquid ammonia for hydrogen generation journal, January 2015

Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives journal, December 2014

Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines Leading to Aromatic Azo Compounds using Dioxygen as an Oxidant journal, July 2010

Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation journal, January 2013

Elusive Terminal Copper Arylnitrene Intermediates journal, May 2017

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

Recent Researches in Triazole Compounds as Medicinal Drugs
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

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

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

A Direct Intramolecular C−H Amination Reaction Cocatalyzed by Copper(II) and Iron(III) as Part of an Efficient Route for the Synthesis of Pyrido[1,2- a ]benzimidazoles from N -Aryl-2-aminopyridines
journal, September 2010

Electrolysis of liquid ammonia for hydrogen generation
journal, January 2015

Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives
journal, December 2014

Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines Leading to Aromatic Azo Compounds using Dioxygen as an Oxidant
journal, July 2010

Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation
journal, January 2013

Elusive Terminal Copper Arylnitrene Intermediates
journal, May 2017

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