ON-SURFACE TRANSFORMATION OF AZIDES

Chemical transformation of 9‐azidophenanthrene on the Ag(111) surface was studied by nc‐AFM in UHV. High‐resolution imaging supported by first‐principle calculations revealed the structure of the final products that originated from a common and elusive 9‐phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ‐ and π‐bonds between their transformation products on a solid surface was demonstrated at a single‐molecule level.

J. Hellerstedt, A. Cahlík, O. Stetsovych, M. Švec, T. K. Shimizu, P. Mutombo, J. Klívar, I.G. Stará, P. Jelínek, I. Starý 
Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy
Angew. Chem. Int. Ed. 58 (2019) 2266 - 2271.