Reductive Deuteration of Aromatic Esters for the Synthesis of α,α-Dideuterio Benzyl Alcohols Using D2O as Deuterium Source
Reductive Deuteration of Aromatic Esters for the Synthesis of α,α-Dideuterio Benzyl Alcohols Using D2O as Deuterium Source
复制标题
以 D2O 为氘源的芳香酯还原氘化合成 α,α-二氘代苯甲醇
DOI：
10.1055/s-0040-1705944
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发表时间：
2020-10-16
期刊：
影响因子：
2
通讯作者：
An, Jie
中科院分区：
文献类型：
--
作者：
Luo, Shihui;Weng, Chaoqun;An, Jie
α，α-二肼基苯甲醇是合成氚标记药物和农用化学品的重要组成部分。我们用温和的单电子给体SmI2和良性的D2O开发了第一个用于合成α，α-二肼基苯甲醇的商用芳香酯的通用单电子转移还原氢化反应。这种操作方便的方法具有非常好的官能团耐受性和高的氘掺入(>；95%D-2)。其潜在的影响已经通过合成许多重要的生物活性化合物的氚标记的积木来例证。最重要的是，该方法代表了第一个使用温和和高化学选择性的稀土(II)试剂选择性还原氢化苄基型酮自由基的例子。
alpha,alpha-Dideuterio benzyl alcohols are important building blocks for the synthesis of deuterium-labeled medicines and agrochemicals. We have developed the first general single-electron transfer reductive deuteration of readily commercially available aromatic esters for the synthesis of alpha,alpha-dideuterio benzyl alcohols using benign D2O and a mild single-electron donor SmI2. This operationally convenient method features very good functional group tolerance and high deuterium incorporations (>95% D-2). The potential impact has been exemplified by the synthesis of numerous deuterium labeled building blocks of important bioactive compounds. Most crucially, the method represents the first example of selective reductive deuteration of benzylic-type ketyl radicals using mild and highly chemoselective lanthanide(II) reagents.