Reduction of alkyl and vinyl sulfonates using the CuCl₂·2H₂O-Li-DTBB(cat.) system

Gabriel Radivoy*, Francisco Alonso, Yanina Moglie, Cristian Vitale and Miguel Yus

*Departamento de Química, Instituto de Investigaciones en Química Orgánica (INIQO), Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina, Email: gradivoycriba.edu.ar

G. Radivoy, F. Alonso, Y. Moglie, C. Vitale, M. Yus, Tetrahedron, 2005, 61, 3859-3864.

DOI: 10.1016/j.tet.2005.01.078

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Abstract

The reduction of a series of alkyl sulfonates to the corresponding hydrocarbons was efficiently performed using a reducing system composed of CuCl₂·2H₂O, an excess of lithium sand and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB), in tetrahydrofuran at room temperature. The process was also applied to enol and dienol triflates affording alkenes and dienes, respectively.

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Key Words

Reduction, Alkyl sulfonates, Enol triflates, Arene catalysis, Active copper, Lithium

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ID: J72-Y2005-2900