Lübcke Marvin, Bezhan Dina, Szabó Kálmán J
Department of Organic Chemistry , Arrhenius Laboratory , Stockholm University , SE-106 91 Stockholm , Sweden . Email:
Chem Sci. 2019 May 6;10(23):5990-5995. doi: 10.1039/c9sc00829b. eCollection 2019 Jun 21.
A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C-SCF and C-C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF group arise from different reagents. Our studies show that the reaction mechanism is similar to the Hooz multicomponent coupling. The process involves generation of BAr, which reacts with a diazocarbonyl compound, and the reaction is terminated by an electrophilic SCF transfer. The reaction can also be extended to fluorination based bifunctionalization which proceeds with somewhat lower yield than the analogous trifluoromethylthiolation reaction.
开发了一种新的基于锌介导的三氟甲硫基化的双官能化反应。在此过程中，在多组分反应中同时发生C-SCF和C-C键形成，其中芳基和SCF基团来自不同的试剂。我们的研究表明，反应机理与胡兹多组分偶联相似。该过程涉及生成BAr，其与重氮羰基化合物反应，并且反应通过亲电SCF转移终止。该反应还可以扩展到基于氟化的双官能化，其产率比类似的三氟甲硫基化反应略低。
