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Pure Appl. Chem., 2003, Vol. 75, No. 10, pp. 1453-1475

Ring opening of heterocycles by an arene-catalyzed lithiation

Miguel Yus

Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo.99, 03080 Alicante, Spain

Abstract: The ring opening of different three-, four-, five-and six-membered oxygen-, nitrogen- and sulfur-containing saturated heterocycles using lithium and a catalytic amount of an arene (naphthalene or DTBB) yields a series of functionalized organolithium compounds, which, by reaction with different electrophiles, allow the preparation of polyfunctionalized molecules in only one synthetic operation.