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Solvent-Free Carbon-Oxygen Bond Formation Catalysed by CeCl3·7 H2O/NaI: Tetrahydropyranylation of Hydroxy Groups

Giuseppe Bartoli, Riccardo Giovannini, Arianna Giuliani, Enrico Marcantoni*, Massimo Massaccesi, Paolo Melchiorre, Melissa Paoletti, Letizia Sambri

*Dipartimento Scienze Chimiche, Universitą di Camerino, via S.Agostino 1, 62032 Camerino, (MC), Italy, Email:

G. Bartoli, R. Giovannini, A. Giuliani, E. Marcantoni, M. Massaccesi, P. Melchiorre, M. Paoletti, L. Sambri, Eur. J. Org. Chem., 2006, 1476-1482.

DOI: 10.1002/ejoc.200500780


A mild, environmentally benign, efficient, and highly chemoselective tetrahydropyranylation of alcohols and phenols is reported, which is catalysed by the CeCl3·7 H2O/NaI system under solvent-free conditions.

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Key Words

Alcohols, Cerium, Lewis acids, Chemoselectivity, Synthetic methods, Protecting groups, Tetrahydropyran ethers

ID: J24-Y2006-850