Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones

• DOI: 10.1021/acs.joc.5b01939
• Publication Date: 2015-10-23T17:26:46Z
• Authors: Maciej E. Domaradzki; Yuhua Long; Zhigang She; Xiaochen Liu; Gan Zhang; Yu Chen
• Keywords: 01 natural sciences; 0104 chemical sciences

An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a intramolecular takes place through two competing mechanisms-a 5-exo-dig or 6-endo-dig cyclization-leading to regioisomeric intermediates: isobenzofuranium isobenzopyrylium. In presence acetate, intermediate compounds undergo further rearrangement 2,3-disubstituted indenones and 1,3-disubstituted isoquinolines, respectively. While both pathways proceed via cyclization-rearrangement cascade, gold-mediated process especially notable, as it provides novel protocol 2-alkynylarylketones.