title: Nucleophilic addition of sulfonamides to bromoacetylenes: facile preparation of pyrroles.
abstract: Nucleophilic addition of sulfonamides to 1-bromo-1-alkynes provided (Z)-N-(1-bromo-1-alken-2-yl)-p-toluenesulfonamides in good yield and in a highly regio- and stereoselective manner. Treatment of product (Z)-N-(1-bromo-1-octen-2-yl)-N-allyl-p-toluenesulfonamide with a palladium catalyst under Heck conditions afforded 1-(p-toluenesulfonyl)-2-hexyl-4-methylpyrrole in good yield. Other pyrroles with various substituents can also be prepared in good yield by this method.
authors.affiliation: Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Kanagawa 226-8501 Japan.
authors.forename: Masahito
authors.initials: M
authors.lastname: Yamagishi
authors.forename: Ken
authors.initials: K
authors.lastname: Nishigai
authors.forename: Takeshi
authors.initials: T
authors.lastname: Hata
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Urabe
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006842:Hydrocarbons, Brominated; D011758:Pyrroles; D013449:Sulfonamides