Synthesis of Functionalized 1H-Indenes and Benzofulvenes through Iodocyclization of o-(Alkynyl)styrenes

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• 作者：Patricia García-GarcíaAna M. Sanjuán ; Muhammad A. Rashid ; Alberto Martínez-Cuezva ; Manuel A. Fernández-Rodríguez ; Félix RodríguezRoberto Sanz
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：82
• 期：2
• 页码：1155-1165
• 全文大小：567K
• ISSN：1520-6904

文摘

A convenient method for the preparation of synthetically useful 3-iodoindene derivatives has been developed. This protocol, based on the 5-endo iodocyclization reaction of o-(alkynyl)styrenes, represents one of the scarce examples of halocyclizations using olefins as nucleophilic counterparts and allows the synthesis of both 3-iodo-1H-indenes (from β-alkyl-β-alkyl/aryl-o-(alkynyl)styrenes) and 3-iodobenzofulvenes (from β,β-diaryl-o-(alkynyl)styrenes) in good yields under mild reaction conditions. In addition, related alkoxyiodocyclization processes are described, which are particularly interesting in their intramolecular version because they allow the synthesis of heteropolycyclic structures containing the indene core. Finally, the usefulness of the prepared 3-iodoindenes has been demonstrated by the synthesis of several polysubstituted indene derivatives through conventional palladium-catalyzed cross-coupling reactions and iodine–lithium exchange processes.