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Updated: Jun 29, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Metal free cross-dehydrogenative N-N coupling of primary amides with Lewis basic amines
Subban Kathiravan1,2, Prakriti Dhillon3, Tianshu Zhang3
1Bioorganic & Biophysical Chemistry Laboratory, Centre for Biomaterials Chemistry, Department of Chemistry & Biomedical Sciences, Linnaeus University, Kalmar, SE-39182, Sweden. suppan.kathiravan@lnu.se.
Abstract:
Hydrazides, N-N containing structural motifs, are important due to their presence in a wide variety of biologically significant compounds. While the homo N-N coupling of two NH moieties to form the hydrazide N-N bond is well developed, the cross-dehydrogenative hetero N-N coupling remains very unevolved. Here we present an efficient intermolecular N-N cross-coupling of a series of primary benzamides with broad range of Lewis basic primary and secondary amines using PhI(OAc)2 as both a terminal oxidant and a cross-coupling mediator, without the need for metal catalysts, high temperatures, and inert atmospheres, and with substantial potential for use in the late-stage functionalization of drugs.
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