Product Manager

Sandra Forbes

Name Reactions

Luche Reduction

The targeted 1,2-reduction of enones is accomplished by employing sodium borohydride in conjunction with CeCl₃.

Mechanism of the Luche Reduction

CeCl₃ serves as a selective Lewis acid catalyst in the methanolysis process of sodium borohydride. The reagents generated through this reaction, namely various sodium methoxyborohydrides, exhibit stronger reducing capabilities (in line with HSAB principles). As a result, they facilitate a 1,2 - reduction with enhanced selectivity.

Furthermore, CeCl₃ activates methanol.

Recent Literature

Under mild reaction conditions, the catalytic enantioselective 1,2-reduction of enones using potassium borohydride is mediated by a chiral N,N'-dioxide-Sc(III) complex catalyst. A variety of optically active allylic alcohols were generated, showcasing excellent enantioselectivities and achieving nearly quantitative yields.

P. He, X. Liu, H. Zheng, W. Li, L. Lin, X. Feng, Org. Lett., 2012, 14, 5134-5137.

DOI: 10.1021/ol302430h

During the reduction of nitroarenes with KBH₄ and I₂, BI₃ is generated in - situ and has been identified as the active reducing agent. The conditions for BI₃ generation were optimized and subsequently applied to a broad spectrum of nitroarenes, encompassing substrates that have traditionally posed challenges. This method presents a practical reduction approach, yielding low-toxicity boric acid and potassium iodide after the work - up process.

A. Ćorković, T. Chiarella, F. J. Williams, Org. Lett., 2023, 25, 8787-8791.

DOI: 10.1021/acs.orglett.3c03257

Quoted from: 

https://www.organic-chemistry.org/chemicals/reductions/potassiumborohydride.shtm

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