Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration
Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration
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高价碘介导的卤化乙烯宝石二氟化反应通过独特的 1,2-卤代迁移实现
DOI：
10.1007/s11426-021-9965-9
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发表时间：
2021-04-06
影响因子：
9.6
通讯作者：
Wang, Honggen
中科院分区：
文献类型：
--
作者：
Li, Chenglong;Liao, Yangzhen;Wang, Honggen
β-二氟化烷基卤化物在偕-二氟化分子的模块合成中具有重要价值。本文报道了一种具有原位生成的PhIF_2中心点HF的卤代乙烯的1，2-卤代迁移性双晶。该方案提供了一种针对多种β-二氟化烷基溴的通用和实用方法。α-和β-溴烷基烯烃都是合适的底物，产生两种不同类型的产物。将该方案扩展到氯乙烯和碘化物也是可行的。该方法的合成多功能性已经通过复杂小分子的后期修饰和β-二氟代烷基卤化物进一步转化为有价值的含CF2化合物而突出。
beta-Difluorinated alkyl halides are of significant value in the modular synthesis of gem-difluorinated molecules. An exclusive 1,2-halo migratory gem-difluorination of vinyl halides with in situ-generated PhIF2 center dot HF is described. This protocol provides a general and practical approach towards a wide variety of beta-difluorinated alkyl bromides. Both alpha- and beta-bromoalkyl alkenes are suitable substrates, leading to two distinct types of products. The extension of this protocol to vinyl chloride and iodide are also feasible. The synthetic versatility of this method has been highlighted by the late-stage modification of complex small molecules and further transformations of the beta-difluorinated alkyl halides to valuable CF2-containing compounds.