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

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:
ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [1]; ORCiD logo [1];  [2]; ORCiD logo [1]
  1. Department of Chemistry, University of Wisconsin–Madison, Madison, USA
  2. Small Molecule Design and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, USA
Publication Date:
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.
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.
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.
@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}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9SC04305E

Save / Share:

Works referenced in this record:


journal, January 2012


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

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

  • 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


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

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


Reactivity of Dioxygen−Copper Systems
journal, February 2004

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

“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

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


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

  • 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


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

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