Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes

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• 作者：Lanlan Zhang ; Yu Geng ; Zhong Jin
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：81
• 期：9
• 页码：3542-3552
• 全文大小：629K
• 年卷期：0
• ISSN：1520-6904

文摘

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.