Mild Chemotriggered Generation of a Fluorophore-Tethered Diazoalkane Species via Smiles Rearrangement.
2016
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.
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