Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light.

Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light.
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DOI:
10.1021/jacs.0c09678
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发表时间:
2020-11-25
影响因子:
15
通讯作者:
Mendoza A
Mendoza A
中科院分区:
化学1区
文献类型:
--
作者:
Chowdhury R;Yu Z;Tong ML;Kohlhepp SV;Yin X;Mendoza A

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已发现光激发二氢烟酰胺(如 NADH 和类似物)在没有辅助光催化剂的情况下,在氧化还原活性酯的还原脱羧作用下产生烷基自由基。这一原理允许氧化还原活性羧酸酯衍生物和贫电子烯烃之间的脂肪族光耦合,显示出令人惊讶的水和空气耐受性以及在稀释条件下异常高的耦合速率。介绍了在其他羧酸存在下反应的正交性及其在 DNA 功能化中的实用性,特别是使用可见光与 NADH(生命中普遍存在的还原剂)相结合。
Photoexcited dihydronicotinamides like NADH and analogues have been found to generate alkyl radicals upon reductive decarboxylation of redox-active esters without auxiliary photocatalysts. This principle allowed aliphatic photocoupling between redox-active carboxylate derivatives and electron-poor olefins, displaying surprising water and air-tolerance and unusually high coupling rates in dilute conditions. The orthogonality of the reaction in the presence of other carboxylic acids and its utility in the functionalization of DNA is presented, notably using visible light in combination with NADH, the ubiquitous reductant of life.
DOI: 10.1021/ja8053805
发表时间: 2008-10-15
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