Journal of Catalysis ( IF 6.5 ) Pub Date : 2022-06-26 , DOI: 10.1016/j.jcat.2022.06.033 Youcan Zhang , Yang Yuan , Hui-Qing Geng , Jian-Xing Xu , Xiao-Feng Wu
Employing a photocatalyst system based on copper and BINAP, visible light-mediated perfluoroalkylative carbonylation of unactivated alkenes has been developed. The method enables a photo-promoted perfluoroalkyl radical addition-carbon monoxide insertion-coupling cascade approach to functionalized β-perfluoroalkyl carbonyl compounds. Various substrates, including alkenes, perfluoroalkyl halides, and nucleophiles (including phenols, alcohols, and amines) are suitable for this tandem procedure, providing more than 70 examples of valuable β-perfluoroalkyl esters and amides with good functional-group tolerance and excellent chemo- and regioselectivity. In addition, late-stage perfluoroalkylative carbonylation of several pharmaceutical and bioactive molecules has been successfully achieved as well.
中文翻译:
可见光诱导的未活化烯烃的全氟烷基化羰基化
采用基于铜和 BINAP 的光催化剂体系,已开发出可见光介导的未活化烯烃的全氟烷基化羰基化。该方法使光促进的全氟烷基自由基加成-一氧化碳插入-偶联级联方法成为功能化的β-全氟烷基羰基化合物成为可能。包括烯烃、全氟烷基卤化物和亲核试剂(包括酚类、醇类和胺类)在内的各种底物都适用于这种串联程序,提供了 70 多个有价值的β-全氟烷基酯和酰胺,具有良好的官能团耐受性和优异的化学和区域选择性。此外,几种药物和生物活性分子的后期全氟烷基化羰基化也已成功实现。