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Published July 6, 2023 | Published + Supplemental Material
Journal Article Open

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

Abstract

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.

Additional Information

© 2023 The Authors. Published by American Chemical Society. Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) The authors thank Corteva Agriscience for funding and scientific discussion, as well as NIH-NIGMS (R01GM080269), NIH-NIGMS (R35GM145239), NIH-NIGMS (R35GM118191), Heritage Medical Research Investigators Program, and Caltech for the support of our research program. Author Contributions. V.N.N. and K.R.S. contributed equally. The authors declare no competing financial interest.

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Published - ja3c04834.pdf

Supplemental Material - ja3c04834_si_001.pdf

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Additional details

Created:
August 22, 2023
Modified:
October 20, 2023