Hydrogen-Isotope Exchange (HIE) Reactions of Secondary and Tertiary Sulfonamides and Sulfonylureas with Iridium(I) Catalysts
Hydrogen-Isotope Exchange (HIE) Reactions of Secondary and Tertiary Sulfonamides and Sulfonylureas with Iridium(I) Catalysts
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DOI：
10.1002/ejoc.201601599
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发表时间：
2017-03-17
影响因子：
2.8
通讯作者：
Derdau, Volker
中科院分区：
文献类型：
--
作者：
Burhop, Annina;Weck, Remo;Derdau, Volker
本文首次报道了多种磺脲类化合物、叔磺酰胺类化合物以及多种仲磺酰胺类化合物选择性芳族氘化反应的最佳氢同位素交换（HIE）条件。通过对现有Ir催化剂的综合筛选，证明kerr型NHC催化剂5在仲磺酰胺和磺脲类的HIE反应中效率最高。然而，对于叔磺胺，市售的伯吉斯催化剂6（尚未用于HIE反应）会导致更高的氘掺入。最后，我们测试了新的HIE方案，用于标记一系列磺胺类药物，并调整了条件，允许选择性标记氚。
For the first time we report the optimized hydrogenisotope exchange (HIE) conditions for the selective aromatic deuteriation of various sulfonylureas and tertiary sulfonamides, as well as for a broad range of secondary sulfonamides. Based on a comprehensive screening of readily available Ir catalysts, the Kerr-type NHC catalyst 5 proved to be most efficient in the HIE reaction of secondary sulfonamides and sulfonylureas. However, for tertiary sulfonamides, the commercially available Burgess catalyst 6, not yet utilized in HIE reactions, resulted in a much higher incorporation of deuterium. Finally, we tested the new HIE protocol for the labelling of a series of sulfa drugs and adapted the conditions to allow for selective tritium labelling.