Das Debabrata, Ghosh Krishna Gopal, Chandu Palasetty, Sureshkumar Devarajulu
Department of Chemical Sciences, Indian Institute of Science Education and Research, Kolkata Mohanpur 741246, West Bengal, India.
J Org Chem. 2020 Nov 6;85(21):14201-14209. doi: 10.1021/acs.joc.0c01752. Epub 2020 Oct 27.
Ammonium chloride-mediated trifluoromethylthiolation of -quinone methides is reported using inexpensive and bench stable AgSCF as a nucleophilic trifluoromethylthiolating (-SCF) reagent. This method is an efficient strategy for the construction of the benzylic C(sp)-SCF bond to synthesize trifluoromethylthio-diarylmethane derivatives by 1,6-conjugate addition/aromatization under mild reaction conditions without any metal catalyst, oxidants, or additives. This is the first report of trifluoromethylthiolation of -quinone methides. In addition, di-trifluoromethylthiolation of δ-chloro--quinone methide and scalability are demonstrated.
报道了使用廉价且易于保存的AgSCF作为亲核三氟甲硫基化试剂（-SCF），通过氯化铵介导的对醌甲基化物进行三氟甲硫基化反应。该方法是构建苄基C(sp)-SCF键的有效策略，可在温和反应条件下，无需任何金属催化剂、氧化剂或添加剂，通过1,6-共轭加成/芳构化反应合成三氟甲硫基二芳基甲烷衍生物。这是关于醌甲基化物三氟甲硫基化反应的首次报道。此外，还展示了δ-氯代-醌甲基化物的双三氟甲硫基化反应及可扩展性。
