Catalytic Regioselective Synthesis of Structurally Diverse Indene Derivatives from N-Benzylic Sulfonamides and Disubstituted Alkynes
journal contributionposted on 03.09.2010, 00:00 authored by Cong-Rong Liu, Fu-Lai Yang, Yi-Zhou Jin, Xian-Tao Ma, Dao-Juan Cheng, Nan Li, Shi-Kai Tian
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 FeCl3-catalyzed cleavage of sp3 carbon−nitrogen bonds to generate benzyl cation intermediates. In the presence of 10 mol % of FeCl3, 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.
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presencealkynyl chalcogenidesSulfonamidedisubstituted alkynesfunctionalized indene derivativesFeClregioselectivityregioselective synthesissulfonamidealkynylcarbonyl compoundsDisubstituted AlkynesCatalytic Regioselective SynthesisStructurally Diverse Indene Derivativesindene derivativesmolalkynyl halidesspcleavagebenzyl cation intermediatesbond