Reductive Cleavage of Secondary Sulfonamides: Converting Terminal Functional Groups into Versatile Synthetic Handles
Reductive Cleavage of Secondary Sulfonamides: Converting Terminal Functional Groups into Versatile Synthetic Handles
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DOI：
10.1021/jacs.9b10985
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发表时间：
2019-11-20
影响因子：
15
通讯作者：
Maloney, Kevin M.
中科院分区：
文献类型：
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作者：
Fier, Patrick S.;Kim, Suhong;Maloney, Kevin M.
磺酰胺在药物和农用化学品中普遍存在，但它们通常被认为是末端官能团而不是合成手柄。为了实现仲磺酰胺的一般后期官能化，我们已经开发了一种温和且通用的方法来还原性地裂解磺酰胺的N-S键以产生亚磺酸酯和胺，这些组分可以进一步原位反应以获得各种其他医学相关的官能团。该平台的实用性突出了几个复杂的生物活性分子的选择性操作。
Sulfonamides are pervasive in pharmaceuticals and agrochemicals, yet they are typically considered as terminal functional groups rather than synthetic handles. To enable the general late-stage functionalization of secondary sulfonamides, we have developed a mild and general method to reductively cleave the N-S bonds of sulfonamides to generate sulfinates and amines, components which can further react in situ to access a variety of other medicinally relevant functional groups. The utility of this platform is highlighted by the selective manipulation of several complex bioactive molecules.