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Metal free cross-dehydrogenative N-N coupling of primary amides with Lewis basic amines.

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.

SUBMITTER: Kathiravan S

PROVIDER: S-EPMC10966042 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Metal free cross-dehydrogenative N-N coupling of primary amides with Lewis basic amines.

Kathiravan Subban S Dhillon Prakriti P Zhang Tianshu T Nicholls Ian A IA

Nature communications 20240326 1

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 ...[more]

PMID: 38531886

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