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Complementary Heterogeneous/Homogeneous Protocols for the Synthesis of Densely Functionalized Benzo[d]sultams: C−C Bond Formation by Intramolecular Nucleophilic Aromatic Fluorine Displacement

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journal contribution
posted on 2008-09-05, 00:00 authored by Michele Penso, Domenico Albanese, Dario Landini, Vittoria Lupi, Aaron Tagliabue
Polyfunctionalized benzo[d]sultams 7 and 8, which contain an α-amino acid unit, have been synthesized from the corresponding open chain (pentafluorobenzene)sulfonamides 4 by complementary solid−liquid phase transfer catalysis (SL-PTC) and homogeneous protocols. The cyclization step proceeds through the intramolecular nucleophilic displacement of an aromatic fluorine atom.