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.michelet
chimie-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
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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
ID: J54-Y2016
