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

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• 作者：Maciej E. Domaradzki ; Yuhua Long ; Zhigang She ; Xiaochen Liu ; Gan Zhang ; Yu Chen
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 20, 2015
• 年：2015
• 卷：80
• 期：22
• 页码：11360-11368
• 全文大小：482K
• ISSN：1520-6904

文摘

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