Nitrene-mediated intermolecular N-N coupling for efficient synthesis of hydrazides

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N-N linkages are found in many natural compounds and endow fascinating structural and functional properties. In comparison to the myriad methods for the construction of C-N bonds, chemistry for N-N coupling, especially in an intermolecular fashion, remains underdeveloped. Here, we report a nitrene-mediated intermolecular N-N coupling of dioxazolones and arylamines under iridium or iron catalysis. These reactions offer a simple and efficient method for the synthesis of various hydrazides from readily available carboxylic acid and amine precursors. Although the Ir-catalysed conditions usually give higher N-N coupling yield than the Fe-catalysed conditions, the reactions of sterically more demanding dioxazolones derived from alpha-substituted carboxylic acids work much better under the Fe-catalysed conditions. Mechanistic studies revealed that the nitrogen atom of Ir acyl nitrene intermediates has strong electrophilicity and can undergo nucleophilic attack with arylamines with the assistance of Cl center dot center dot center dot HN hydrogen bonding to form the N-N bond with high efficiency and chemoselectivity.
Publisher
NATURE RESEARCH
Issue Date
2021-04
Language
English
Article Type
Article
Citation

NATURE CHEMISTRY, v.13, no.4

ISSN
1755-4330
DOI
10.1038/s41557-021-00650-0
URI
http://hdl.handle.net/10203/283674
Appears in Collection
CH-Journal Papers(저널논문)
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