Cong Liu, Fulai Yang, Yi Jin
Aug 4, 2010
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Organic letters
Abstract
An unprecedented protocol has been developed for the regioselective synthesis of structurally diverse indene derivatives from readily accessible N-benzylic sulfonamides and disubstituted alkynes through FeCl(3)-catalyzed cleavage of sp(3) carbon-nitrogen bonds to generate benzyl cation intermediates. In the presence of 10 mol % of FeCl(3), a broad range of N-benzylic sulfonamides smoothly react with internal alkynes, alkynylcarbonyl compounds, alkynyl chalcogenides, or alkynyl halides to afford various functionalized indene derivatives with extremely high regioselectivity.