N-heterocylic carbene boryl azides are a new, stable class of electronically rich azides. Under refluxing or microwave conditions, boryl azides were reacted with electron poor alkynes, alkenes, and nitriles to form stable boryl triazoles, triazolidines, and tetrazoles respectively by [3 +2]-dipolar cycloaddition. Cycloaddition products were purified by column chromatography and characterized by NMR spectroscopy and X-Ray crystallography. Both 1,4 and 1,5 boryl triazoles and triazolidines were formed from cycloaddition of boryl azide and alkynes or alkenes. Only 1,5 boryl tetrazoles were formed from the cycloaddition of nitriles and boryl azide.

N-heterocyclic carbene boryl azide [2 + 3]-dipolar cycloadditions with electron deficient alkynes, alkenes, and nitriles

246th National Meeting (2013)

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