title: Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes.
abstract: An efficient and transition-metal-free N-arylation of amides via the insertion of arynes into the N-H bonds in the N-alkoxy amides is described. A variety of the reactive functional groups including the reactive aldehyde carbonyl group, furan ring, carbon-carbon double bonds, and free N-H bond of indole are found to be compatible with this process. In particular, the protocol is applicable in the synthesis of structurally diverse N-aryl hydroxamates and hydroxamic acids derived from N-protecting amino acids and peptides. In the presence of multiple amide N-H bonds, the N-arylation reaction can proceed selectively in the N-H bonds of terminal N-OBn amides giving rise to the desired N-aryl hydroxamates.
authors.affiliation: State Key Laboratory of Elementoorganic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Lanlan
authors.initials: L
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Elementoorganic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Geng
authors.affiliation: State Key Laboratory of Elementoorganic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Zhong
authors.initials: Z
authors.lastname: Jin