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Site-Selective Deuteration of N-Heterocycles via Iridium-Catalyzed Hydrogen Isotope Exchange
ACS Catalysis ( IF 11.3 ) Pub Date : 2017-09-25 00:00:00 , DOI: 10.1021/acscatal.7b02682
William J. Kerr 1 , David M. Lindsay 1 , Philippa K. Owens 1 , Marc Reid 1 , Tell Tuttle 1 , Sebastien Campos 2
Affiliation  

The application of iridium(I) NHC/phosphine catalysts has delivered highly selective deuteration of indole, azaindole, and pyrrole N-heterocycles, which represent an important and relatively underexplored class of labeling substrates. Common N-protecting groups have been used to selectively direct C–H activation and can be removed under mild conditions with retention of the deuterium label. The method is exemplified by the labeling of the drug molecule sumatriptan. Complementary DFT studies have been conducted to facilitate the rationalization of the very good selectivity offered by the mild and convenient labeling process.

中文翻译:

通过铱催化的氢同位素交换对N-杂环进行位点选择性氘化

铱(I)NHC /膦催化剂的应用已使吲哚,氮杂吲哚和吡咯N-杂环具有高度选择性的氘化,这代表了一种重要的且相对未开发的标记底物。常用的N保护基团已被用来选择性地引导C–H活化,可以在温和条件下除去氘标记而将其除去。该方法以药物分子舒马曲坦的标记为例。已经进行了补充DFT研究,以促进合理和方便的标记过程提供的非常好的选择性的合理化。
更新日期:2017-09-25
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