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

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

Creators

  • 1. ROR icon California Institute of Technology

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.

Attached Files

Published - ja3c04834.pdf

Supplemental Material - ja3c04834_si_001.pdf

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Additional details

Identifiers

PMCID
PMC10360072
Eprint ID
122448
Resolver ID
CaltechAUTHORS:20230725-856879000.13

Funding

NIH
R01GM080269
NIH
R35GM145239
NIH
R35GM118191
Heritage Medical Research Institute
Caltech

Dates

Created
2023-08-16
Created from EPrint's datestamp field
Updated
2023-08-16
Created from EPrint's last_modified field

Caltech Custom Metadata

Caltech groups
Heritage Medical Research Institute