title: Diverse methyl sulfone-containing benzo[b]thiophene library via iodocyclization and palladium-catalyzed coupling.
abstract: Parallel solution-phase methods for the synthesis of a 72-membered benzo[b]thiophene library are reported. Medicinally interesting, drug-like, methyl sulfone-substituted benzo[b]thiophenes have been prepared by the palladium-catalyzed substitution of 3-iodobenzo[b]thiophenes by Suzuki-Miyaura, Sonogashira, Heck, carboalkoxylation, and aminocarbonylation chemistry. The key intermediates for library generation, methyl sulfone-containing 3-iodobenzo[b]thiophenes, are readily prepared by iodocyclization and oxidation methodologies from readily available alkynes.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
authors.forename: Chul-Hee
authors.initials: CH
authors.lastname: Cho
authors.forename: Benjamin
authors.initials: B
authors.lastname: Neuenswander
authors.forename: Richard C
authors.initials: RC
authors.lastname: Larock
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D013450:Sulfones; D013876:Thiophenes; C088015:benzothiophene; D010165:Palladium; D007455:Iodine; C025910:dimethyl sulfone; D004121:Dimethyl Sulfoxide