title: A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.
abstract: Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.
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: Hikaru
authors.initials: H
authors.lastname: Fujita
authors.forename: Munetaka
authors.initials: M
authors.lastname: Kunishima
mesh_terms: D000143:Acids / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D002384:Catalysis; D005960:Glucosides / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000143:Acids; D005960:Glucosides; D001554:Benzene