Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides

[Image: see text] A nickel-catalyzed N–N cross-coupling for the synthesis of hydrazides is reported. O-Benzoylated hydroxamates were efficiently coupled with a broad range of aryl and aliphatic amines via nickel catalysis to form hydrazides in an up to 81% yield. Experimental evidence implicates the...

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Autores principales: Barbor, Jay P., Nair, Vaishnavi N., Sharp, Kimberly R., Lohrey, Trevor D., Dibrell, Sara E., Shah, Tejas K., Walsh, Martin J., Reisman, Sarah E., Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10360072/
https://www.ncbi.nlm.nih.gov/pubmed/37413695
http://dx.doi.org/10.1021/jacs.3c04834
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author Barbor, Jay P.
Nair, Vaishnavi N.
Sharp, Kimberly R.
Lohrey, Trevor D.
Dibrell, Sara E.
Shah, Tejas K.
Walsh, Martin J.
Reisman, Sarah E.
Stoltz, Brian M.
author_facet Barbor, Jay P.
Nair, Vaishnavi N.
Sharp, Kimberly R.
Lohrey, Trevor D.
Dibrell, Sara E.
Shah, Tejas K.
Walsh, Martin J.
Reisman, Sarah E.
Stoltz, Brian M.
author_sort Barbor, Jay P.
collection PubMed
description [Image: see text] A nickel-catalyzed N–N cross-coupling for the synthesis of hydrazides is reported. O-Benzoylated hydroxamates were efficiently coupled with a broad range of aryl and aliphatic amines via nickel catalysis to form hydrazides in an up to 81% yield. Experimental evidence implicates the intermediacy of electrophilic Ni-stabilized acyl nitrenoids and the formation of a Ni(I) catalyst via silane-mediated reduction. This report constitutes the first example of an intermolecular N–N coupling compatible with secondary aliphatic amines.
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spelling pubmed-103600722023-07-22 Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides Barbor, Jay P. Nair, Vaishnavi N. Sharp, Kimberly R. Lohrey, Trevor D. Dibrell, Sara E. Shah, Tejas K. Walsh, Martin J. Reisman, Sarah E. Stoltz, Brian M. J Am Chem Soc [Image: see text] A nickel-catalyzed N–N cross-coupling for the synthesis of hydrazides is reported. O-Benzoylated hydroxamates were efficiently coupled with a broad range of aryl and aliphatic amines via nickel catalysis to form hydrazides in an up to 81% yield. Experimental evidence implicates the intermediacy of electrophilic Ni-stabilized acyl nitrenoids and the formation of a Ni(I) catalyst via silane-mediated reduction. This report constitutes the first example of an intermolecular N–N coupling compatible with secondary aliphatic amines. American Chemical Society 2023-07-06 /pmc/articles/PMC10360072/ /pubmed/37413695 http://dx.doi.org/10.1021/jacs.3c04834 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Barbor, Jay P.
Nair, Vaishnavi N.
Sharp, Kimberly R.
Lohrey, Trevor D.
Dibrell, Sara E.
Shah, Tejas K.
Walsh, Martin J.
Reisman, Sarah E.
Stoltz, Brian M.
Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
title Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
title_full Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
title_fullStr Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
title_full_unstemmed Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
title_short Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
title_sort development of a nickel-catalyzed n–n coupling for the synthesis of hydrazides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10360072/
https://www.ncbi.nlm.nih.gov/pubmed/37413695
http://dx.doi.org/10.1021/jacs.3c04834
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