铜催化的未活化烯烃烯基化反应中，脱硫酰基引发的远端烯基迁移。
Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes.
机构信息
Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science , Tianjin University , Tianjin 300072 , P. R. China.
Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology , Tianjin University , Tianjin 300072 , P. R. China.
出版信息
Org Lett. 2018 Oct 19;20(20):6516-6519. doi: 10.1021/acs.orglett.8b02840. Epub 2018 Oct 4.
A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroalkylalkenylation of unactivated alkenes with excellent chemo-, regio-, and stereoselectivity in high efficiency under mild conditions. The reactions afford previously unknown 3,3-difluoro-5-styrylpiperidin-2-one derivatives or β-styryl-γ-difluoroalkyl amines bearing a quaternary stereocenter. This is the first report of difunctionalization of unactivated alkenes through desulfonylation-initiated distal alkenyl migration.
本文提出了一种新颖、高效的脱磺酰基引发远程烯基迁移反应的方法，并将其应用于难以实现的非活化烯烃的烯基化反应。该自由基级联反应在温和条件下以优异的化学选择性、区域选择性和立体选择性高效地实现了非活化烯烃的偕二氟烷基烯基化反应。反应得到了以前未知的 3,3-二氟-5-苯乙烯基哌啶-2-酮衍生物或带有季立体中心的β-苯乙烯基-γ-二氟烷基胺。这是首例通过脱磺酰基引发远程烯基迁移实现非活化烯烃双官能化的报道。
Zotero 插件