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

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Title
Nitrene-mediated intermolecular N–N coupling for efficient synthesis of hydrazides
Author(s)
Hao Wang; Hoimin Jung; Fangfang Song; Shiyang Zhu; Ziqian Bai; Danye Chen; Gang He; Sukbok Chang; Gong Chen
Publication Date
2021-04
Journal
Nature Chemistry, v.13, pp.378 - 385
Publisher
Nature Research
Abstract
© 2021, The Author(s), under exclusive licence to Springer Nature Limited.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 α-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···HN hydrogen bonding to form the N–N bond with high efficiency and chemoselectivity. [Figure not available: see fulltext.]
URI
https://pr.ibs.re.kr/handle/8788114/9549
DOI
10.1038/s41557-021-00650-0
ISSN
1755-4330
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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