title: Hydroamination and hydroalkoxylation catalyzed by triflic acid. Parallels to reactions initiated with metal triflates.
abstract: Intermolecular additions of the O-H bonds of phenols and alcohols and the N-H bonds of sulfonamides and benzamide to olefins catalyzed by 1 mol % of triflic acid and studies to define the relationship between these reactions and those catalyzed by metal triflates are reported. Cyclization of an alcohol containing pendant monosubstituted and trisubstituted olefins catalyzed by either triflic acid or metal triflates form products from addition to the more substituted olefin, and additions of tosylamide catalyzed by triflic acid or metal triflates form indistinguishable ratios of the two N-alkyl sulfonamides.
authors.affiliation: Department of Chemistry, Yale University, PO Box 208107, New Haven, Connecticut 6520-8107, USA.
authors.forename: Devon C
authors.initials: DC
authors.lastname: Rosenfeld
authors.forename: Shashank
authors.initials: S
authors.lastname: Shekhar
authors.forename: Akihiro
authors.initials: A
authors.lastname: Takemiya
authors.forename: Masaru
authors.initials: M
authors.lastname: Utsunomiya
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*
chemical_list: D000473:Alkanes; D008698:Mesylates; D008670:Metals; C012077:trifluoromethanesulfonic acid