Direct and Scalable Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine,Journal of the American Chemical Society

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Direct and Scalable Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-01-16 , DOI: 10.1021/jacs.9b12112
Shuhei Manabe ₁ , Curt M Wong ₁ , Christo S Sevov ₁

Affiliation

The direct and scalable electroreduction of triphenylphosphine oxide (TPPO) - the stoichiometric byproduct of some of the most common synthetic organic reactions - to triphenylphosphine (TPP) remains an unmet challenge that would dramatical-ly reduce costs and waste associated with performing desirable reactions that are mediated by TPP on large scale. This report details an electrochemical methodology for the single-step reduction of TPPO to TPP using an aluminum anode in combina-tion with a supporting electrolyte that continuously regenerates a Lewis acid from the products of anodic oxidation. The re-sulting Lewis acid activates TPPO for reduction at mild potentials and promotes P-O over P-C bond cleavage to selectively form TPP over other byproducts. Finally, this robust methodology is applied to (i) the reduction of synthetically useful classes of phosphine oxides, (ii) the one-pot recycling of TPPO generated from a Wittig reaction, and (iii) the gram-scale reduction of TPPO at high concentration (1 M) with continuous product extraction and in flow at high current density.

中文翻译：

三苯基氧化膦直接和可扩展的电还原为三苯基膦

将氧化三苯膦 (TPPO)（一些最常见的合成有机反应的化学计量副产物）直接和可扩展地电还原为三苯膦 (TPP) 仍然是一个未解决的挑战，它将显着降低与执行所需反应相关的成本和浪费由 TPP 进行大规模调解。该报告详细介绍了使用铝阳极与支持电解质相结合的将 TPPO 单步还原为 TPP 的电化学方法，该电解质可从阳极氧化产物中连续再生路易斯酸。产生的路易斯酸在温和的电位下激活 TPPO 进行还原，并促进 PO 通过 PC 键断裂选择性地形成 TPP，而不是其他副产物。最后，

更新日期：2020-01-16

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