title: Regioselective formation of tetrahydroselenophenes via 5-exo-dig-cyclization of 1-butylseleno-4-alkynes.
abstract: Results on the synthesis of tetrahydroselenophene derivatives from 1-butylseleno-4-alkynes by electrophilic cyclization using iodine as the electrophilic source are presented. This methodology was carried out via a simple process under mild reaction conditions providing the cyclized products in high yields. Electrophilic sources, such as PhSeBr, CuCl(2), and CuBr(2), were also used in this study. The tetrahydroselenophenes obtained by this protocol were submitted to cyanation, Suzuki, and Ullmann cross-coupling reactions to afford good yields of a cross-coupled product.
authors.affiliation: Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul, Brazil, 97105-900.
authors.forename: Rafaela M
authors.initials: RM
authors.lastname: Gai
authors.forename: Ricardo F
authors.initials: RF
authors.lastname: Schumacher
authors.forename: Davi F
authors.initials: DF
authors.lastname: Back
authors.forename: Gilson
authors.initials: G
authors.lastname: Zeni
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D006846:Hydrocarbons, Halogenated; D016566:Organoselenium Compounds