It has been previously shown that hypervalent iodonium alkynyl triflates (HIATs) can be reacted with azide sources to produce cyanocarbenes. The azide attacks the electrophilic �-?carbon of the alkyne to create an iodo-?ylide which rearranges to an alkynyl azide. The alkynyl azide decomposes to a cyanocarbene which is trapped with solvents or other substrates. In this work, two in-situ preparations are described one of which utilizes catalytic Cu(II) to potentially bypass unwanted side-products.

In-situ method for the generation and trapping of cyanocarbenes formed from alkynes and azides

248th National Meeting (2014)

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