Mild Chemotriggered Generation of a Fluorophore-Tethered Diazoalkane Species via Smiles Rearrangement

In
situ generation of diazoalkanes under mild conditions is desired.
A mechanism based on a Smiles rearrangement has been devised that
releases a fluorophore-labeled unstabilized diazoalkane in the presence
of various chemical triggers. Notably, the release of this diazoalkane
is accompanied by an intense fluorescence turn-on, which calibrates
the release of the diazoalkane. Carboxylic acids can trap this short-lived
diazoalkane intermediate and yield the corresponding esters. This
transformation has potential for broad applications.