Nickel-catalyzed site-selective amidation of unactivated C(sp 3)-H bonds

Xuesong Wu, Yan Zhao, Haibo Ge

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105 Scopus citations

Abstract

Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel-catalyzed C-H bond functionalization process with the assistance of a bidentate directing group. The reaction favors the C-H bonds of β-methyl groups over the γ-methyl or β-methylene groups. Additionally, a predominant preference for the β-methyl C-H bonds over the aromatic sp2 C-H bonds was observed. Moreover, this process also allows for the effective functionalization of benzylic secondary sp3 C-H bonds. β-Lactams from nickel catalysis: Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel-catalyzed C-H bond functionalization process with the assistance of a bidentate directing group (see scheme).

Original languageEnglish
Pages (from-to)9530-9533
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number31
DOIs
StatePublished - Jul 28 2014

Keywords

  • C-H bond functionalization
  • amidation
  • nickel
  • site selectivity
  • β-lactams

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