Over the past decade, click chemistry has drawn great interest in the scientific community. The most popular reaction of click chemistry is the [3+2] cycloaddition of alkynes with azides via copper-catalyzed azide-alkyne cycloaddition (CuAAC) or strain-promoted alkyne-azide cycloaddition (SPAAC). Recently, our group has developed and employed alkynogenic fragmentation chemistry to produce strain cycloalkynes (benzocyclononyes) which has shown improved stability to its cyclooctyne counterparts. Tethered to the benzocylcononynes are terminal alkynes producing a unique diyne that provides the first example of a so-called “dual-click” coupling via CuAAC or SPAAC in either sequential order. The resulting bis-triazoles provide CBz-type functionality that offer an optional <i>ex post facto</i> de-coupling of the diyne system.

Orthogonal dual-click diyne for CuAAC and/or SPAAC couplings

253rd National Meeting (2017)

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