DOI: 10.1021/acs.orglett.6c03340 ISSN: 1523-7060
Copper-Catalyzed Formal [5 + 1] Annulation of Diynes with 1 H -Indole-2-ethanols: Construction of Tetrahydropyrano Indoles
Yin-Zhu Kong, Chen-Yong Weng, Fu-Wen Tan, Maxim A. Novikov, Roman A. Novikov, Gongde Wu, Fu-Shuai Li, Bo Zhou, Long-Wu YeAbstract
Transition-metal-catalyzed annulation of diynes with nucleophiles is a powerful tool for constructing valuable complex (hetero)cycles. However, reports on the cascade annulation of diynes with dinucleophiles are rare and confined to noble-metal catalysts, narrow diyne scopes, and specific reaction types. Herein, we describe a copper-catalyzed formal [5 + 1] annulation of 1,6-diynes with 1H-indole-2-ethanols via vinyl cations, leading to the concise and practical synthesis of tetrahydropyrano indoles. Significantly, this protocol represents the first non-noble-metal-catalyzed annulation of diynes with dinucleophiles.