943-52-2Relevant academic research and scientific papers
Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes
Lin, Jin-Hong,Xiao, Ji-Chang,Yang, Yi-Fei
supporting information, p. 9277 - 9282 (2021/12/06)
In contrast with unactivated alkenes, the corresponding hydrotrifluoromethylation of styrene has remained challenging due to the strong propensity of styrene for oligomerization and polymerization. On the basis of our newly developed trifluoromethylation reagent, TFSP, herein we present a general method for the hydrotrifluoromethylation of styrene under photoredox catalysis. The substrate scope was further extended to unactivated alkenes, acrylates, acrylamides, and vinyl-heteroatom-substituted alkenes. The tunability of this method was showcased via the relevant deprotonative trifluoromethylation and trifluoromethyltrifluoroethoxylation reactions.
Method for preparing fluoroalkane substituted compound by reducing halogenated fluoroalkane and olefin through metal elementary substance
-
Paragraph 0061-0069; 0275-0283, (2021/07/17)
The invention discloses a method for preparing a fluoroalkane substituted compound, which comprises the steps of taking a compound containing carbon-carbon double bonds and halogenated fluoroalkane as raw materials, taking a metal elementary substance as a reducing agent, taking a substance containing active protons as a hydrogen source, and carrying out an addition reaction to prepare a compound which is simultaneously substituted by hydrogen and fluoroalkyl, thereby obtaining the fluoroalkane substituted compound. According to the method, the metal elementary substance is used as the reducing agent for the first time, the compound containing active hydrogen is used as the hydrogen source, one hydrogen atom and one fluoroalkyl group are introduced to the two ends of olefin respectively, only one-step reaction is needed, the reaction process conditions are mild, the reaction raw materials are cheap and easy to obtain, the cost is low, and all reaction reagents are green and environmentally friendly; and the reaction substrate has strong applicability, can participate in the reaction as long as carbon-carbon double bonds exist in the structure, and is not influenced by the types of substituent groups on carbon atoms of the double bonds, and the yield of the product is good.
Copper-Catalyzed Trifluoromethylation of Alkyl Bromides
Kornfilt, David J.P.,Macmillan, David W.C.
supporting information, p. 6853 - 6858 (2019/05/10)
Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.
Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
Kautzky, Jacob A.,Wang, Tao,Evans, Ryan W.,Macmillan, David W. C.
supporting information, p. 6522 - 6526 (2018/05/25)
Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, al
Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow
Straathof, Natan J. W.,Cramer, Sten E.,Hessel, Volker,No?l, Timothy
supporting information, p. 15549 - 15553 (2016/12/09)
Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.
