Mao Runze, Bera Srikrishna, Cheseaux Alexis, Hu Xile
Laboratory of Inorganic Synthesis and Catalysis , Institute of Chemical Sciences and Engineering , École Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI , Lausanne 1015 , Switzerland . Email:
Chem Sci. 2019 Aug 26;10(41):9555-9559. doi: 10.1039/c9sc03396c. eCollection 2019 Nov 7.
Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an "umpolung" strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation.
在此，我们描述了一种脱氧三氟甲硫基化方法，该方法可从易得的羧酸制备三氟甲硫酯。该方法基于一种“极性翻转”策略，其中三苯基膦首先用于活化亲电三氟甲硫基化试剂，然后作为脱氧反应的氧受体。该方法温和、高效、适用范围广且耐受性好。它可用于许多含有羧酸基团的天然产物和药物分子的后期官能团化。三氟甲硫酯可通过钯催化的脱羰反应转化为三氟甲硫醚。
