5172-99-6Relevant academic research and scientific papers
Benzyltrifluoromethyl (or Fluoroalkyl) Selenide: Reagent for Electrophilic Trifluoromethyl (or Fluoroalkyl) Selenolation
Glenadel, Quentin,Ismalaj, Ermal,Billard, Thierry
, p. 8268 - 8275 (2016)
Trifluoromethylseleno substituent (CF3Se) is an emerging group, but its direct introduction onto organic molecules is still quite limited and mainly restricted to nucleophilic methods. Herein, we describe a new approach to easily and safely perform electrophilic trifluoromethylselenolation starting from a simple and easily accessible reagent, namely, benzyltrifluoromethyl selenide. This strategy can be generalized to various fluoroalkylselanyl groups, even functionalized ones.
Using fluoroform for constructing aromatic and heterocyclic trifluoromethylselenyl compounds
Aharon, Cheryl,Rozen, Shlomo
, (2021/09/10)
Fluoroform is used to prepare CuCF3 according to literature procedures. This nucleophilic trifluoromethyl moiety was reacted with aromatic and heterocyclic selenium cyanide derivatives to form the corresponding trifluoromethylselenium compounds. Selenium cyanides were made with 1,3-dicyanotriselenide prepared in situ from malononitrile and selenium dioxide. The electrophilicity of the reagent (δ+SeCN) was enough to attack aniline derivatives at the para position, but with other aromatics it was advantageous to use the corresponding boronic acid as the moiety was easily displaced by the selenium cyanate moiety.
Trifluoromethylselenolation of Aryldiazonium Salts: A Mild and Convenient Copper-Catalyzed Procedure for the Introduction of the SeCF3 Group
Nikolaienko, Pavlo,Rueping, Magnus
, p. 2620 - 2623 (2016/02/27)
The straightforward introduction of the trifluoromethylseleno group into aromatic and heteroaromatic compounds is accomplished by the utilization of readily available aryldiazonium tetrafluoroborates, potassium selenocyanate, and Ruppert-Prakash reagent. The reaction tolerates a wide range of aromatic and heteroaromatic diazonium salts and is also amenable to the synthesis of pentafluoroethyl selenoethers. Furthermore, the methodology can be applied directly starting from anilines.
General synthesis of trifluoromethyl selenides utilizing selenocyanates and fluoroform
Potash, Shay,Rozen, Shlomo
, p. 11205 - 11208 (2015/02/19)
Trifluoromethylated selenoethers are quite rare despite their potential and the interest that they generate. A series of trifluoromethylseleno derivatives, either primary and secondary aliphatic or aromatic and heterocyclic, is described herein by the reaction of easily prepared organic selenocyanates and CuCF3. Another beneficial feature of this reaction is the use of fluoroform as a source for the CF3 group, a compound whose chemistry is currently being intensively researched because it is a potent greenhouse gas that should not be released into the atmosphere.
