Copper‐Catalyzed Reductive N‐Alkylation of Amides with N‐Tosylhydrazones Derived from Ketones. Issue 14 (27th June 2016)

• Record Type: Journal Article
• Authors: Xu, Peng; Qi, Fu‐Ling; Han, Fu‐She; Wang, Yan‐Hua
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 14(2016)
• Page Start: 2030
• Page End: 2034
• Publication Date: 2016-06-27
• Subjects: amides -- copper catalysts -- ketones -- N-tosylhydrazones -- reductive coupling; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600733
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: A CuI‐catalyzed reductive coupling of ketone‐derived N ‐tosylhydrazones with amides is presented. Under the optimized conditions, an array of N ‐tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hetero)aryl as well as aliphatic amides to afford the N ‐alkylated amides in high yields. The method represents the very few examples for reliably accessing secondary and tertiary amides through a reductive N ‐alkylation protocol. Abstract : A CuI‐catalyzed reductive coupling of ketone‐derived N ‐tosylhydrazones with amides has been developed (see scheme). Under the optimized conditions, an array of N ‐tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hetero)aryl as well as aliphatic amides to afford the N ‐alkylated amides in high yields. The method represents the very few examples for reliably accessing secondary and tertiary amides through a reductive N ‐alkylation protocol.