Air, moisture and thermal stable triazapentalene Zwitterion compounds were prepared through Au(I) catalyzed triazole-alkyne 5-endo-dig cyclization.  The reaction was highly efficient with up to 96% isolated yield (0.5% catalyst loading).  The introduction of electron-withdrawing groups on the triazole-ring not only helped to achieve the effective gold catalyst turnover, but also improved the stability of those compounds.

Synthesis and characterization of a novel 10-electron system with unique zwitterion formation

244th National Meeting (2012)

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