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

Ryan, Michael C.; Kim, Yeon Jung; Gerken, James B.; Wang, Fei; Aristov, Michael M.; Martinelli, Joseph R.; Stahl, Shannon S.

doi:10.1039/C9SC04305E

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

Abstract

Catalytic N–N coupling is a valuable transformation for chemical synthesis and energy conversion. Here, mechanistic studies are presented for two related copper-catalyzed oxidative aerobic N–N coupling reactions, one involving the synthesis of a pharmaceutically relevant triazole and the other relevant to the oxidative conversion of ammonia to hydrazine. Analysis of catalytic and stoichiometric N–N coupling reactions support an “oxidase”-type catalytic mechanism with two redox half-reactions: (1) aerobic oxidation of a Cu^I catalyst and (2) Cu^II-promoted N–N coupling. Both reactions feature turnover-limiting oxidation of Cu^I by O₂, and this step is inhibited by the N–H substrate(s). The results highlight the unexpected facility of the N–N coupling step and establish a foundation for development of improved catalysts for these transformations.

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

Research Org.:: Univ. of Wisconsin, Madison, WI (United States)

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

OSTI Identifier:: 1579758

Alternate Identifier(s):: OSTI ID: 1800250

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

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

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.  https://doi.org/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.  https://doi.org/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 = {Catalytic N–N coupling is a valuable transformation for chemical synthesis and energy conversion. Here, mechanistic studies are presented for two related copper-catalyzed oxidative aerobic N–N coupling reactions, one involving the synthesis of a pharmaceutically relevant triazole and the other relevant to the oxidative conversion of ammonia to hydrazine. Analysis of catalytic and stoichiometric N–N coupling reactions support an “oxidase”-type catalytic mechanism with two redox half-reactions: (1) aerobic oxidation of a CuI catalyst and (2) CuII-promoted N–N coupling. Both reactions feature turnover-limiting oxidation of CuI by O2, and this step is inhibited by the N–H substrate(s). The results highlight the unexpected facility of the N–N coupling step and establish a foundation for development of improved catalysts for these transformations.},

  doi          = {10.1039/C9SC04305E},

  journal      = {Chemical Science},

  number       = 4,

  volume       = 11,

  place        = {United Kingdom},

  year         = {2020},

  month        = {1}

}

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

Abstract

Citation Formats

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Hydrazine Production from Ammonia via Azine
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Copper-catalyzed oxidative coupling of diphenylmethanimine promoted by some monodentate pyridines*1
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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
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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
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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