Domański Sylwester, Gatlik Beata, Chaładaj Wojciech
Institute of Organic Chemistry , Polish Academy of Sciences , Kasprzaka 44/52 , 01-224 Warsaw , Poland.
Org Lett. 2019 Jul 5;21(13):5021-5025. doi: 10.1021/acs.orglett.9b01618. Epub 2019 Jun 24.
A three-component tandem Pd-catalyzed perfluoroalkylative borylation of terminal and internal alkynes is presented. On the basis of this methodology, the first reductive dicarbofunctionalization of alkynes with two electrophiles (perfluoroalkyl and aryl iodides) through a temperature-controlled sequence of iodoperfluoroalkylation-borylation coupling is developed. This regio- and stereoselective process is easily controllable by a temperature program, providing access to fluoroalkyl-substituted vinyl iodides, vinyl boronates, or olefins from the very same complex reaction mixture (four substrates, catalysts, base, and additives).
本文报道了一种三组分串联钯催化的末端炔烃和内炔烃的全氟烷基硼化反应。基于该方法，通过碘全氟烷基化-硼化偶联的温控序列，首次实现了炔烃与两种亲电试剂（全氟烷基碘化物和芳基碘化物）的还原双碳官能化反应。该区域和立体选择性过程可通过温度程序轻松控制，能从同一复杂反应混合物（四种底物、催化剂、碱和添加剂）中获得氟烷基取代的乙烯基碘化物、硼酸乙烯酯或烯烃。
