Direct Synthesis\nof Saturated Alcohols from Conjugated\nKetones Using NaBH<sub>4</sub> and Catalytic Amount of CuCN in Ethanol:\nAdditive Catalysis with a Lithium Salt or a Sodium Salt

A direct, efficient, and highly chemoselective synthesis\nof saturated\nalcohols through one-pot sequential 1,4- and 1,2-reduction of cyclic\nand acyclic conjugated ketones is reported. The saturated alcohols\nare obtained in very good yields using sodium borohydride (NaBH<sub>4</sub>) as a reducing agent and a catalytic amount of copper(I)\ncyanide (CuCN) in ethanol as a green solvent. This nontoxic solvent\nsignificantly favors full 1,4-reduction, as opposed to methanol. Selectivity\nis further enhanced by the combination of two additives (a lithium\nsalt or a sodium salt, such as NaI).

Publication Details

Journal
Figshare
Published
2024-10-16
DOI
https://doi.org/10.1021/acs.joc.4c01564.s001
Primary Topic
German Social Sciences and History
Type
article
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article

Direct Synthesis\nof Saturated Alcohols from Conjugated\nKetones Using NaBH4 and Catalytic Amount of CuCN in Ethanol:\nAdditive Catalysis with a Lithium Salt or a Sodium Salt

Figshare
German Social Sciences and History
article

Direct Synthesis\nof Saturated Alcohols from Conjugated\nKetones Using NaBH4 and Catalytic Amount of CuCN in Ethanol:\nAdditive Catalysis with a Lithium Salt or a Sodium Salt

article en

Abstract

A direct, efficient, and highly chemoselective synthesis\nof saturated\nalcohols through one-pot sequential 1,4- and 1,2-reduction of cyclic\nand acyclic conjugated ketones is reported. The saturated alcohols\nare obtained in very good yields using sodium borohydride (NaBH<sub>4</sub>) as a reducing agent and a catalytic amount of copper(I)\ncyanide (CuCN) in ethanol as a green solvent. This nontoxic solvent\nsignificantly favors full 1,4-reduction, as opposed to methanol. Selectivity\nis further enhanced by the combination of two additives (a lithium\nsalt or a sodium salt, such as NaI).

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German Social Sciences and History
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Direct Synthesis\nof Saturated Alcohols from Conjugated\nKetones Using NaBH<sub>4</sub> and Catalytic Amount of CuCN in Ethanol:\nAdditive Catalysis with a Lithium Salt or a Sodium Salt · Figshare (2024) | TGRS Research Map | TGRS