title: Synthesis of Polysubstituted 2-Iodoindenes via Iodonium-Induced Cyclization of Arylallenes.
abstract: A new chemoselective iodocarbocyclization of allenyl arenes was developed leading to the formation of 2-iodoindenes. In acetonitrile or nitromethane, electrophilic sources of iodine cations react selectively with the C2-C3 double bond of 1-arylallenes to give, after anti nucleophilic attack of the aromatic ring, 2-iodoindene products in high yields. Variations of the allenic skeletons revealed the high 5-endo selectivity and some competitive pathways of cyclization. Postfunctionalization reactions of the carbon-iodine bond, via Pd- and Cu-cross-couplings, gave rise to substituted indenes in good to excellent yields.
authors.affiliation: PSL Research University , Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, F-75005 Paris, France.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Grandclaudon
authors.affiliation: PSL Research University , Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, F-75005 Paris, France.
authors.forename: Véronique
authors.initials: V
authors.lastname: Michelet
authors.affiliation: PSL Research University , Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, F-75005 Paris, France.
authors.forename: Patrick Y
authors.initials: PY
authors.lastname: Toullec