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

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.