PPh3 催化的醛到醇的化学选择性还原

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2024-09-30 DOI:10.1016/j.tetlet.2024.155317
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引用次数: 0

摘要

将醛还原成醇是一种基本的有机转化,通常通过金属催化还原或使用氢化物试剂来实现。然而,这些传统方法通常需要在苛刻的条件下使用昂贵的催化剂和额外的还原剂,从而限制了其更广泛的应用。在本研究中,我们首次介绍了一种在 MeOH 中使用三苯基膦 (PPh3) 和 KOtBu 的高效无金属还原策略。这种方法具有广泛的官能团耐受性、温和的环境以及还原醛的选择性,即使存在其他活性官能团(NO2、CN、酮等)也不例外。这种新方法的主要特点是实用性强、可扩展至克级规模,而且在将各种醛还原为醇时产量极高(30 个实例;产量为 65-95 %)。
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PPh3-catalyzed chemoselective reduction of aldehydes to alcohols
Reduction of aldehydes to alcohols is a fundamental organic transformation, typically achieved through metal-catalyzed reductions or by the use of hydride-based reagents. However, these conventional methods often go through harsh conditions with expensive catalysts and additional reductants, limiting their broader applications. In this study, for the first time we introduce an efficient, metal-free reduction strategy using triphenylphosphine (PPh3) and KOtBu in MeOH. This method exhibits broad functional group tolerance, mild environment and selectivity in reducing aldehydes even in the presence of other reactive functionalities (NO2, CN, ketone, etc.). Key features highlight this novel approach with practicality, scalability to gram scales and excellent yields for the reduction of varied aldehydes to alcohols (30 examples; 65–95 % Yields).
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来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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