Due to their appealing physiological attributes, tertiary aliphatic amines are pervasive in a myriad of biologically active molecules. In particular, amines featuring homoallylic substituents serve as versatile synthetic building blocks. Therefore, there is a growing demand for the development of practical and modular methods for the rapid assembly of sp³-rich complex amines from readily accessible chemical feedstock. Here, we disclose a multicomponent, reductive photocatalytic protocol that merges secondary alkylamines, carbonyl compounds, and fluoroalkyl-substituted alkenes, yielding fluorinated tertiary aliphatic homoallylamines. This defluorinative aminoalkylation protocol involves the addition of alkyl-substituted α-amino radicals, generated from reduction of in situ-generated iminium ions by a photocatalyst, to fluoroalkyl-substituted alkenes and subsequent fluoride elimination, reliably furnishing gem-difluoroalkene and monofluoroalkene motifs that are not easily accessible through alternative methods. Utility of the method was demonstrated by its broad functional group compatibility, the derivatization of complex alkylamines, and the synthesis of drug analogues.

中文翻译：

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通过氟烷基取代烯烃的光催化脱氟氨烷基化反应获得氟化叔高烯丙胺

由于其有吸引力的生理特性，脂肪族叔胺普遍存在于无数生物活性分子中。特别是，具有同烯丙基取代基的胺可作为通用的合成结构单元。因此，对于开发实用和模块化方法以从容易获得的化学原料快速组装富含sp ³的复杂胺的需求不断增长。在这里，我们公开了一种多组分还原光催化方案，该方案合并仲烷基胺、羰基化合物和氟烷基取代的烯烃，产生氟化叔脂肪族高烯丙胺。这种脱氟氨基烷基化方案涉及将烷基取代的α-氨基自由基（通过光催化剂原位还原产生的亚胺离子产生）添加到氟烷基取代的烯烃中，然后消除氟化物，可靠地提供宝石-二氟烯烃和单氟烯烃基序。通过替代方法不容易获得。该方法的实用性通过其广泛的官能团兼容性、复杂烷基胺的衍生化以及药物类似物的合成得到证明。