title: Development of a new benzylating reagent spontaneously releasing benzyl cation equivalents at room temperature.
abstract: A new O-benzylating reagent, that is, 4-(4,6-diphenoxy-1,3,5-triazin-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate (DPT-BM), has been developed. Benzyl cation equivalents are generated from DPT-BM by dissolving the compound in a solvent at room temperature under non-acidic conditions. The benzylation of various alcohols by using a combination of DPT-BM and magnesium oxide provided the benzyl ethers in good yields.
authors.affiliation: Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan).
authors.forename: Kohei
authors.initials: K
authors.lastname: Yamada
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Tsukada
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Karuo
authors.forename: Masanori
authors.initials: M
authors.lastname: Kitamura
authors.forename: Munetaka
authors.initials: M
authors.lastname: Kunishima
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D015394:Molecular Structure; D013696:Temperature
chemical_list: D001555:Benzene Derivatives; D002412:Cations
keywords: alkylation; carbocations; protecting groups; reaction mechanisms; synthetic methods