title: Synthesis of Substituted Benzenes via Bi(OTf)3-Mediated Intramolecular Carbonyl Allylation of α-Prenyl or α-Geranyl β-Arylketosulfones.
abstract: Intramolecular carbonyl allylation of α-prenyl or α-geranyl β-arylketosulfones 5 in the presence of molecule sieves (MS) affords substituted benzenes 6-7 in moderate to good yields. The facile transformation proceeds by a synthetic sequence starting with the α-prenylation or α-geranylation of 1 and the Bi(OTf)3-mediated annulation of 5 followed by a sequential desulfonative aromatization or then an intramolecular Friedel-Crafts alkylation. A plausible mechanism has been studied and proposed.
authors.affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
authors.forename: Meng-Yang
authors.initials: MY
authors.lastname: Chang
authors.affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
authors.forename: Yu-Chieh
authors.initials: YC
authors.lastname: Cheng
authors.affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
authors.forename: Yi-Ju
authors.initials: YJ
authors.lastname: Lu
mesh_terms: D000478:Alkylation; D001554:Benzene / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009387:Neoprene / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D008698:Mesylates; D013438:Sulfhydryl Compounds; C016077:prenyl; C445789:Bi(OTf)3; D009387:Neoprene; D001554:Benzene