ORGN 315 |
| More than 125 years after its inception, electrophilic aromatic substitution (the Friedel-Crafts reaction) still remains a popular methodology for C-C bond formation and is the subject of intense investigation today. Friedel-Crafts reactions traditionally require stoichiometric amounts of strong Lewis acids and severe conditions. Additionally, Friedel-Crafts reactions with electron deficient arenes remain a formidable challenge. Therefore, efficient, mild, and catalytic methods to activate electrophiles for Friedel-Crafts reactions are highly significant. Recently, we have demonstrated an unusual halogen atom transfer cyclization catalyzed by In(III) Lewis acids which proceeded via activation of an allylic bromide. Even though there are a number of cationic halogen activations known using stoichiometric Lewis acids, we have shown In(III) is capable of activating allilic halides catalytically in non-donor solvents. Herein, we disclose the results of our intramolecular Friedel-Crafts cycliization to prepare carbo- and hetero-benzocycles by catalytic halide activation under remarkably mild conditions.
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Metal-Mediated Reactions and Syntheses
1:00 PM-5:00 PM, Monday, 11 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
