Direct Synthesis of Saturated Alcohols from Conjugated Ketones Using NaBH<sub>4</sub> and Catalytic Amount of CuCN in Ethanol: Additive Catalysis with a Lithium Salt or a Sodium Salt
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<sub>4</sub>) 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).
Authors
- Fabrice Thomas (ORCID: https://orcid.org/0000-0002-6977-5192)
- Cyrille Sabot (ORCID: https://orcid.org/0000-0002-5014-7217)
- Florian Berthiol (ORCID: https://orcid.org/0000-0002-2253-3401)
- Jean‐Pierre Deprés (ORCID: https://orcid.org/0000-0003-1937-9981)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Département de Chimie Moléculaire (FR)
- Normandie Université (FR)
- Laboratoire COBRA (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
- Université Grenoble Alpes (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-16
- DOI
- https://doi.org/10.1021/acs.joc.4c01564
- Citations
- 3
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.48
Funders
- Université Grenoble Alpes
- LABoratoires d’EXcellence ARCANE
- Agence Nationale de la Recherche
- Centre National de la Recherche Scientifique