通过钯催化的 o-卤代苯乙烯和 o-卤代烯丙基苯的芳炔环化反应合成 9-芴酮和 9,10-菲。
Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
J Org Chem. 2009 Dec 4;74(23):9132-9. doi: 10.1021/jo9017827.
Abstract
A number of functionally substituted 9-fluorenylidenes and 9,10-phenanthrenes have been synthesized from substituted o-halostyrenes and o-halo allylic benzenes respectively in good yields by the palladium-catalyzed annulation of arynes. The methodology tolerates a variety of functional groups, including cyano, ester, aldehyde, and ketone groups, occurs under relatively mild reaction conditions, and involves the generation of two new carbon-carbon bonds, thus providing these important carbocyclic ring systems in a single synthetic step.
摘要
通过钯催化的芳基炔烃的环化反应，分别从取代的 o-卤代苯乙烯和 o-卤代烯丙基苯出发，高产率地合成了许多功能取代的 9-芴基和 9,10-菲基。该方法可以容忍多种官能团，包括氰基、酯基、醛基和酮基，反应条件相对温和，并且涉及两个新的碳-碳键的生成，因此可以在单个合成步骤中提供这些重要的碳环系统。
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