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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


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.

Attached Files

Published - ja3c04834.pdf

Supplemental Material - ja3c04834_si_001.pdf


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August 22, 2023
October 20, 2023