Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water,Organic Letters

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Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water
Organic Letters ( IF 4.9 ) Pub Date : 2018-04-05 00:00:00 , DOI: 10.1021/acs.orglett.8b00778
Rui Wang ₁ , Mengyue Ma ₁ , Xu Gong ₁ , Grace B. Panetti ₂ , Xinyuan Fan ₁ , Patrick J. Walsh _{1,

2}

Affiliation

A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D₂O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.

中文翻译：

亚胺的可见光介导的Uppolung反应性：与Cy ₂ NMe和水的Ketimine还原

证明了由光氧化还原催化介导的亚胺的新型碳负离子反应性。可以通过从水中提取质子作为将苯甲酮酮亚胺还原为胺的关键步骤（高达98％的收率）来说明umpolung亚胺的反应性。使用D ₂ O作为廉价的氘源（≥95％D比）将氘有效地引入胺中。探讨了这种异常转变的机制。

更新日期：2018-04-05

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