Trifluoromethanesulfonyl azide as a bifunctional reagent for metal-free azidotrifluoromethylation of unactivated alkenes.
Trifluoromethanesulfonyl azide as a bifunctional reagent for metal-free azidotrifluoromethylation of unactivated alkenes.
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三氟甲磺酰叠氮化物作为双功能试剂用于未活化烯烃的无金属叠氮基三氟甲基化
DOI：
10.1039/d0sc06473d
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发表时间：
2021-01-07
期刊：
影响因子：
8.4
通讯作者：
Liu WB
中科院分区：
文献类型：
--
作者：
Huang HG;Li W;Zhong D;Wang HC;Zhao J;Liu WB
邻位三氟甲基叠氮化合物在有机合成和药物开发中有着广泛的应用。然而，它们的制备一般局限于过渡金属催化的三组分反应。我们在这里报告了一种简单且不含金属的方法，它可以快速地从丰富的烯烃和三氟甲基磺酰叠氮(N3SO2CF3)中提供这些构建块。这一史无前例的双组分反应使用了现成的N3SO2CF3作为双官能团试剂，同时结合了CF3和N3基团，从而避免了使用昂贵且低原子的经济前体。广泛的官能团，包括生物相关的杂环和氨基酸，都是可以容忍的。该方法的应用进一步通过放大合成(5 Mmol)，产物衍生化含CF3的药物化学基元，以及对天然产物和药物衍生物的后期修饰。利用易于合成的三氟甲基磺酰叠氮(N3SO2CF3)作为CF3和N3基团的双功能试剂，实现了烯烃的双组分无金属叠氮三氟甲基化反应。
Vicinal trifluoromethyl azides have widespread applications in organic synthesis and drug development. However, their preparation is generally limited to transition-metal-catalyzed three-component reactions. We report here a simple and metal-free method that rapidly provides these building blocks from abundant alkenes and trifluoromethanesulfonyl azide (N3SO2CF3). This unprecedented two-component reaction employs readily available N3SO2CF3 as a bifunctional reagent to concurrently incorporate both CF3 and N3 groups, which avoids the use of their expensive and low atom economic precursors. A wide range of functional groups, including bio-relevant heterocycles and amino acids, were tolerated. Application of this method was further demonstrated by scale-up synthesis (5 mmol), product derivatization to CF3-containing medicinal chemistry motifs, as well as late-stage modification of natural product and drug derivatives. A two-component and metal-free azidotrifluoromethylation of alkenes is realized using readily synthesized trifluoromethanesulfonyl azide (N3SO2CF3) as a bifunctional reagent for both CF3 and N3 groups.
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