Transition-Metal-Free C–O or C–N Bond Formation Reactions from α-Ketosulfonyl Hydrazones with Alkyl Halides or Amines
Abstract
Diazo compounds can easily generate reactive ketenes by the Wolff rearrangement and construct diverse functionalized skeletons. Here, we describe a metal-free C-O or C-N bond formation reaction from readily available and stable α-ketosulfonyl hydrazones with alkyl halides or amines. Furthermore, the reaction demonstrated a broad substrate scope and afforded functionalized α,α-disubstituted esters or amides in up to 97% yields, respectively. The practical utility of this synthetic strategy was further demonstrated by gram-scale syntheses and subsequent derivatization. The preliminary mechanism studies suggest that the reaction proceeds via the initial generation of reactive ketene intermediates, followed by a nucleophilic attack pathway.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Chemical synthesis and pharmacological studies
Organic Chemistry Synthesis Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 4
- Pages
- 1555–1562
- Publication date
- 16 January 2026
- Language
- EN