1226575-23-0Relevant 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
supporting information, 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.
Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine
Dolfen, Jeroen,Kenis, Sara,Van Hecke, Kristof,De Kimpe, Norbert,D'Hooghe, Matthias
, p. 10650 - 10653 (2014/09/16)
This paper reports on the generation and alkylation of the 1-tosyl-2-(trifluoromethyl)aziridin-2-yl anion with ω,ω′- dihaloalkanes, followed by a novel ring-expansion protocol toward 2-CF 3-pyrrolidines, 2-CF3-piperidines, and 3-CF 3-azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF3-azaheterocycles bearing different types of functionalized side chains. CF3-azaheterocycles: The alkylation of the 1-tosyl-2-(trifluoromethyl)aziridin-2-yl anion with ω,ω′- dihaloalkanes, followed by a novel ring-expansion protocol leads to 2-CF 3-pyrrolidines, 2-CF3-piperidines, and 3-CF 3-azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF3-azaheterocycles bearing different types of functionalized side chains (see scheme; HMPA=hexamethylphosphoramide, Ts=para-toluenesulfonyl).
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
