Synthesis 2003(3): 0443-0447
DOI: 10.1055/s-2003-37357
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reduction of Carbonyl Compounds and Imines Using the CuCl2·2H2O-Li-DTBB (Cat.) Combination

Francisco Alonsoa, Cristian Vitaleb, Gabriel Radivoy*b, Miguel Yus*a
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Fax: +34(96)5903549; e-Mail: yus@ua.es;
Instituto de Investigaciones en Química Orgánica (INIQO), Departamento de Química, Universidad Nacional del Sur, Avda. Alem 1253, 8000 Bahía Blanca, Argentina
Fax: +54(29)14595187; e-Mail: gradivoy@criba.edu.ar;
Further Information

Publication History

Received 26 November 2002
Publication Date:
19 February 2003 (online)

Abstract

The reaction of different carbonyl compounds and imines­ with a mixture of copper(II) chloride dihydrate, an excess of lithium sand, and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding alcohols and amines, respectively. The process was also applied to the transformation of α,β-unsaturated carbonyl compounds into the corresponding saturated alcohols. The use of the deuterated copper salt CuCl2·2D2O allowed the preparation of the corresponding deuterated products.