MnBr2-Catalyzed Aerobic Oxyazidation of Fluoroolefins: Access to Fluoroalkylated β-Hydroxy Aliphatic Azides,Advanced Synthesis & Catalysis

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MnBr2-Catalyzed Aerobic Oxyazidation of Fluoroolefins: Access to Fluoroalkylated β-Hydroxy Aliphatic Azides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-01-17 , DOI: 10.1002/adsc.202201254
Yingying Cai ₁ , Huanfeng Jiang ₁ , Chuanle Zhu ₁

Affiliation

MnBr₂-catalyzed oxyazidation of fluoroolefins with molecular oxygen and TMSN₃ is reported. This method gives rise to various useful fluoroalkylated β-hydroxy aliphatic azides in 36%–97% yields. Importantly, this protocol features mild conditions, operationally simple, and gram-scalable, it tolerates various functional groups and has been applied in the synthesis of diverse attractive bioactive compounds and analogous. Mechanism studies enable the detection of the intermediate and indicate that a radical reaction process is involved. The β-fluoride elimination of α-fluoroalkylated radicals via radical-polar crossover pathway was completely inhibited in this reaction.

中文翻译：

MnBr2 催化的氟烯烃有氧叠氮化反应：获得氟烷基化 β-羟基脂肪族叠氮化物

报道了MnBr ₂催化的氟代烯烃与分子氧和 TMSN ₃的叠氮化反应。该方法以 36%–97% 的收率产生各种有用的氟烷基化 β-羟基脂肪族叠氮化物。重要的是，该协议具有温和的条件、操作简单和克级可扩展性，它可以容忍各种功能组，并已应用于各种有吸引力的生物活性化合物和类似物的合成。机理研究能够检测到中间体，并表明涉及一个自由基反应过程。α-氟烷基化自由基通过自由基-极性交叉途径的β-氟化物消除在该反应中被完全抑制。

更新日期：2023-01-17

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