Synthesis and Isolation of α-Diazophosphonium Ylides
Abstract
Well-controlled generation and utilization of phosphorus-ylide-stabilized diazo compounds remain largely unexplored, despite their potential applications. Here, we report a general strategy that transforms Bestmann ylide derivatives into α-diazophosphonium ylide, triazole, or thiadiazole derivatives via reactions with organo-azides, enabling the first isolation of α-diazophosphonium ylide, species that combines the properties of classical ylides with diazo functionality. Its reactivity was examined with diverse E–H bonds across the p -block elements. DFT studies elucidate the factors governing product selectivity and the unique charge distribution that determines the subsequent reactivity. This work establishes α-diazophosphonium ylide as a new entry point into diazo chemistry and opens avenues for future applications in synthesis.
Fields of Study & Subjects
Phosphorus compounds and reactions
Organophosphorus compounds synthesis
Synthesis and Reactivity of Sulfur-Containing Compounds
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 12
- Pages
- 12495–12501
- Publication date
- 20 March 2026
- Language
- EN