Work

Direct Synthesis of Saturated Alcohols from Conjugated Ketones Using NaBH4 and Catalytic Amount of CuCN in Ethanol: Additive Catalysis with a Lithium Salt or a Sodium Salt

Year: 2024

Type: article

Abstract: A direct, efficient, and highly chemoselective synthesis of saturated alcohols through one-pot sequential 1,4- and 1,2-reduction of cyclic and acyclic conjugated ketones is reported. The saturated alcohols are obtained in very good yields using sodium borohydride (NaBH 4 ) as a reducing agent and a catalytic amount of copper(I) cyanide (CuCN) in ethanol as a green solvent. This nontoxic solvent significantly favors full 1,4-reduction, as opposed to methanol. Selectivity is further enhanced by the combination of two additives (a lithium salt or a sodium salt, such as NaI).

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01564

Authors: Florian Berthiol, Fabrice Thomas, Cyrille Sabot, Jean-Pierre Deprés