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Updated: May 5, 2026
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
In Crystallo Synthesis of a Triplet Silver Nitrene
Pritam Roychowdhury1, Aishanee Sur1, Matthew T Figgins1
1Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
None:
Reactive silver nitrenes are proposed intermediates in Ag-catalyzed C-H amination and olefin aziridination reactions. Synthesis and characterization of reactive Ag nitrenes has proven elusive due to fleeting lifetimes and argentophilic aggregation of Ag(I) precursors in solution. Here, we report the templated in crystallo synthesis and characterization of a mononuclear Ag nitrene supported by a tris(pyrazolyl)borate ligand. Photolytic N2 elimination from the corresponding aryl azide complex yields a structurally defined Ag nitrene with a triplet ground state, as confirmed by crystallography, magnetic measurements, and quantum chemical calculations. This species displays both stoichiometric and catalytic nitrene transfer reactivity, enabling carbazole and indole formation from organic azides. These results leverage in crystallo templating to isolate a mononuclear triplet nitrene of Ag and provide a platform to experimentally elucidate ligand-controlled selectivity in Ag-catalyzed nitrene transfer catalysis.
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