842142-04-5Relevant articles and documents
Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents
Liu, Guokai,Mori, Satoru,Wang, Xin,Noritake, Shun,Tokunaga, Etsuko,Shibata, Norio
supporting information; experimental part, p. 1769 - 1773 (2012/10/08)
A series of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts 1 were readily synthesized by treatment of corresponding (bromodifluoromethyl) arylsulfoxides 2 and substituted benzenes 3 with triflic anhydride in moderate to good yields. The unsymmetrical sulfonium salts 1 with different aryl groups having electron-donating or electron-withdrawing substituents can be nicely constructed depending on the choice of 2 and 3. Bromodifluoromethylation of alkynes was evaluated by using the selected diarylsulfonium salts 1 to provide the desired bromodifluoromethylated alkynes in moderate to good yields.
New electrophilic bromodifluoromethylation and pentafluoroethylation reagents
Zhang, Cheng-Pan,Cao, Hai-Ping,Wang, Zong-Ling,Zhang, Chun-Tao,Chen, Qing-Yun,Xiao, Ji-Chang
supporting information; experimental part, p. 1089 - 1092 (2010/06/21)
S-(fluoroalkyl)diphenylsulfonium salts have been successfully synthesized from the reaction between fluoroalkylsul-finates and triflic anhydride in dichloromethane through a one-pot procedure. These S-(fluoroalkyl) diphenylsulfonium salts have been demonstrated to be effective reagents to fluoroalkylate C-nucleophilic substrates. Ionic substitution and radical or halogenophilic mechanism might be all involved in the reactions. Georg Thieme Verlag Stuttgart - New York.
Nucleophilic and electrophilic substitutions of difluoropropargyl bromides
Hammond, Gerald B.
, p. 476 - 488 (2008/03/14)
Fundamental organic reactions like nucleophilic and electrophilic substitutions have seldom been studied on fluorinated propargyl or allenyl modules, when the carbon atom undergoing substitution is bonded to two fluorine atoms. Herein we report a practical synthesis of difluoropropargyl bromides from substituted acetylenes and dibromodifluorometane using a wide variety of alkyl, aryl or silyl substrates. The synthesis of O-, S- and carboxylic acid derivatives of difluoropropargyl bromide is also described. These compounds are suitable starting materials for the synthesis of electrophilically substituted difluoropropargyl derivatives via magnesium and fluoride promoted reactions. An indium-mediated reaction of silyldifluoropropargyl bromide, followed by electrophilic trapping with bromine led to a very useful bromoallene, which was then used in reactions with nucleophiles (C, O, N, P, S, Hal) to yield a de facto bimolecular nucleophilic substitution of a difluoropropargyl bromide.