The formation of alkynyl azides has long been sought after for use in chemical synthesis, but even when formed they rapidly decompose to cyanocarbenes. Previous literature reports have investigated the generation of cyanocarbenes from sodium azide and alkynyl halides but were plagued by long reaction times and low yields. In this work, the synthesis of hypervalent iodonium alkynyl triflates creates an electrophilic alkyne which is then attacked by the addition of a nucleophilic azide source. The reaction goes through several intermediates which ultimately form the cyanocarbene and iodobenzene. The cyanocarbene is then trapped by the reaction with solvent or other molecules. Several trapping substrates and hypervalent iodonium alkynyl triflates are discussed.

Utilization of hypervalent iodonium alkynyl triflates for the generation of cyanocarbenes

243rd National Meeting (2012)

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