811-68-7Relevant articles and documents
Downs, A. J.,Ebsworth, E. A. V.,Emeleus, H. J.
, (1962)
Ammonium Chloride-Mediated Trifluoromethylthiolation of p-Quinone Methides
Das, Debabrata,Ghosh, Krishna Gopal,Chandu, Palasetty,Sureshkumar, Devarajulu
, p. 14201 - 14209 (2020/11/13)
Ammonium chloride-mediated trifluoromethylthiolation of p-quinone methides is reported using inexpensive and bench stable AgSCF3 as a nucleophilic trifluoromethylthiolating (-SCF3) reagent. This method is an efficient strategy for the construction of the benzylic C(sp3)-SCF3 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 p-quinone methides. In addition, di-trifluoromethylthiolation of δ-chloro-p-quinone methide and scalability are demonstrated.
Direct sequential C-H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: A new protocol for potent trypanocidal quinones
Jardim, Guilherme A. M.,Oliveira, Willian X. C.,De Freitas, Rossimiriam P.,Menna-Barreto, Rubem F. S.,Silva, Thaissa L.,Goulart, Marilia O. F.,Da Silva Júnior, Eufranio N.
supporting information, p. 1686 - 1691 (2018/03/21)
We report a sequential C-H iodination/organoyl-thiolation of naphthoquinones and their relevant trypanocidal activity. Under a combination of AgSR with a copper source, sulfur-substituted benzenoid quinones were prepared in high yields (generally >90%). This provides an efficient and general method for preparing A-ring modified naphthoquinoidal systems, recognized as a challenge in quinone chemistry.