A Novel Acid-Catalyzed O-Benzylating Reagent with the Smallest Unit of Imidate Structure
Kohei Yamada, Hikaru Fujita and Munetaka Kunishima*
*Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 Japan, Email: kunisimap.kanazawa-u.ac.jp
K. Yamada, H. Fujita, M. Kunishima, Org. Lett., 2012, 14, 5026-5029.
DOI: 10.1021/ol302222p (free Supporting Information)
Inexpensive stable crystalline 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT) 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 benzyl ethers in good yields. TriBOT, which is the formal trimerization of the smallest unit of benzyl imidate, offers high atom economy.
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