Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation

Abstract

Robust NHC-palladacycles (NHC = N-heterocyclic carbene) were synthesized and exhibited high catalytic activity towards Suzuki−Miyaura cross-coupling reactions between inactive amides with N-acetyl/benzyl substituents and aryl boronic acids, producing diverse ketones in good to excellent yields. This unprecedented and practical palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides with boronic acids via selective C-N bond activation was attributed to the strong σ-donor and weak π-acceptor properties of acenaphthoimidazolylidene, which may highlight their potential in other challenging coupling transformations involving inactive amides.

Keywords

• Aryl boronic acids
• C-N activation
• Inactive amides
• NHC-Palladacycle
• Suzuki−Miyaura cross-coupling