title: Hydroxy-directed, fluoride-catalyzed epoxide hydrosilylation for the synthesis of 1,4-diols.
abstract: A novel highly regioselective, fluoride-catalyzed hydrosilylation of β-hydroxy epoxides has been developed. The reaction is modular and applicable to the synthesis of a broad range of 1,4-diols. Fluoride is crucial for two reasons: First, it promotes the formation of a silyl ether (which contains a Si-H bond) and, second, it enables ring opening by an intramolecular S(N)2 reaction through activation of the silane. The reaction can be performed under air.
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk Strasse 1, 53121 Bonn (Germany).
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Zhang
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk Strasse 1, 53121 Bonn (Germany).
authors.forename: Nico
authors.initials: N
authors.lastname: Funken
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk Strasse 1, 53121 Bonn (Germany).
authors.forename: Peter
authors.initials: P
authors.lastname: Winterscheid
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk Strasse 1, 53121 Bonn (Germany). andreas.gansaeuer@uni-bonn.de.
authors.forename: Andreas
authors.initials: A
authors.lastname: Gansäuer
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004852:Epoxy Compounds; D012821:Silanes; D005459:Fluorides
keywords: 1,4-diols; epoxide opening; fluoride catalysis; hydrosilylation; regioselectivity