An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate a-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.