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Synthesis of Polysubstituted 2-Iodoindenes via Iodonium-Induced Cyclization of Arylallenes

Charlotte Grandclaudon, Véronique Michelet* and Patrick Y. Toullec*

*PSL Research University, Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, F-75005 Paris, France, Email: veronique.micheletchimie-paristech.fr, patrick.toullecu-bordeaux.fr

C. Grandclaudon, V. Michelet, P. Y. Toullec, Org. Lett., 2016, 18, 676-679.

DOI: 10.1021/acs.orglett.5b03634 (free Supporting Information)



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Abstract

A chemoselective iodocarbocyclization of allenyl arenes provides 2-iodoindenes in high yields in the presence of NIS as source of iodine cations in acetonitrile or nitromethane. Variations of the allenic skeletons revealed the high 5-endo selectivity and some competitive pathways of cyclization. Pd- and Cu-catalyzed postfunctionalization reactions of the carbon-iodine bond enable the synthesis of substituted indenes in good yields.


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Key Words

indenes


ID: J54-Y2016