A gold-catalyzed, nucleophile-controlled cascade reaction of -(2-azidophenyl-ynyl)methanesulfonamides with nitriles and water is described that provides structurally diverse 5-pyrimido[5,4-]indoles and 2-benzylidene-3-indolinones in good to excellent yields. Mechanistic studies indicate that the β-sulfonamido-α-imino gold carbene is the key intermediate which is generated through the gold-catalyzed cyclization of -(2-azidophenyl-ynyl)methanesulfonamides and undergoes formal [4 + 2] cascade annulation with nitriles and intramolecular S2' type reaction with water, respectively.
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