Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 9, Pages 3542-3552Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00111
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Funding
- National Natural Science Foundation of China (NNSFC) [21172111]
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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.
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