1226575-11-6Relevant academic research and scientific papers
Design of Trifluoroalkenyl Iodonium Salts for a Hypervalency-Aided Alkenylation–Cyclization Strategy: Metal-Free Construction of Aziridine Rings
Mészáros, ádám,Székely, Anna,Stirling, András,Novák, Zoltán
, p. 6643 - 6647 (2018/06/11)
The synthesis of fluorinated compounds and their use as pharmaceutical ingredients or synthetic building blocks have been in the focus of chemical and medicinal research. However, the efficient synthesis of trifluoromethylated nitrogen heterocycles is sometimes challenging. Herein, we disclose a simple aziridination process that relies on the use of amines and novel alkenyl iodonium reagents for the synthesis of strained, trifluoromethylated heterocycles. With the utilization of a newly designed and bench-stable but highly reactive hypervalent alkenyl iodonium species, these three-membered-ring heterocyclic compounds can be efficiently constructed from simple amines under mild conditions in the absence of transition-metal catalysts. The special reactivity of the new trifluoropropenyl synthon towards nucleophilic centers could be exploited in more general cyclization and alkenylation reactions in the future.
Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone
Kenis, Sara,D'Hooghe, Matthias,Verniest, Guido,Nguyen, Vinh Duc,Thi, Tuyet Anh Dang,Nguyen, Tuyen Van,Kimpe, Norbert De
, p. 7217 - 7223 (2011/11/06)
An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, α-chlorination, hydride reduction and ring closure was developed. In addition, novel primary β-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel α-CF3-β-phenylethylamines upon treatment with lithium diphenylcuprate.
Preparation and reactions of (β-trifluoromethyl)vinyl sulfonium salt
Maeda, Ryoko,Ooyama, Kyoko,Anno, Ryoko,Shiosaki, Masahiro,Azema, Takayuki,Hanamoto, Takeshi
supporting information; experimental part, p. 2548 - 2550 (2010/07/20)
(β-Trifluoromethyl)vinyl sulfonium salt as a novel three-carbon fluorinated building block was conveniently prepared from easily available (β-trifluoromethyl)vinyl sulfide and diphenyl iodonium salt in excellent yield. This easily handled crystalline reag
