928658-43-9Relevant academic research and scientific papers
HFO-1234yf as a CF3-Building Block: Synthesis and Chemistry of CF3-Ynones
Murray, Ben J.,Marsh, Thomas G. F.,Yufit, Dmitri S.,Fox, Mark A.,Harsanyi, Antal,Boulton, Lee T.,Sandford, Graham
supporting information, p. 6236 - 6244 (2020/09/15)
Reaction of low cost, readily available 4th generation refrigerant gas 2,3,3,3-tetrafluoropropene (HFO-1234yf) with lithium diisopropylamide (LDA) leads to formation of lithium 3,3,3-trifluoropropynide, addition of which to a range of aldehydes formed CF3-alkynyl alcohol derivatives on multigram scale, which were oxidised using Dess–Martin periodinane (DMP) to give substituted CF3-ynones with minimal purification required. Michael-type additions of alcohol and amine nucleophiles to CF3-ynones are rapid and selective, affording a range of CF3-enone ethers and enaminones in excellent yields with high stereoselectivity for the Z-isomer. By analogous reactions with difunctional nucleophiles, a wide range of CF3-substituted pharmaceutically relevant heterocyclic structures can be accessed, exemplified in the simple synthesis of the anti-arthritis drug celecoxib from HFO-1234yf in just three steps.
Highly Enantioselective [3 + 2] Annulation of 3-Butynoates with β-Trifluoromethyl Enones Promoted by an Amine-Phosphine Binary Catalytic System
Ding, Kuiling,Han, Zhaobin,Lu, Yixin,Ni, Huanzhen,Wong, Yee Lin,Wu, Mingyue
supporting information, (2020/03/30)
We report a highly enantioselective [3 + 2] annulation between 3-butynoates and β-trifluoromethyl enones, furnishing trifluoromethylated cyclopentenes with three contiguous stereogenic centers in good yields, high diastereoselectivities, and excellent enantioselectivities. A unique catalytic system consisting of a simple amine and a chiral phosphine was devised, and the synergistic play of Lewis basic amine and phosphine was crucial for alkyne isomerization and subsequent cyclization. The protocol disclosed herein allows facile activation of 3-butynoates in phosphine-mediated asymmetric transformations.
Iron-Catalyzed Thiocyclization for the Synthesis of Trifluoro-methylated Benzothiophenes by C-H Functionalization of Aryl Disulfides
Lin, Yan-Feng,Wang, Chong,Hu, Bo-Lun,Qian, Peng-Cheng,Zhang, Xing-Guo
supporting information, p. 707 - 712 (2017/03/21)
An iron-catalyzed thiocyclization of propynols with aryl disulfides has been developed for the synthesis of trifluoromethylated benzothiophenes. The one-pot tandem reaction involves Meyer-Schuster -rearrangement of propynols and radical cyclization through C-H functionalization of aryl disulfides. A variety of 2-trifluoroacyl benzothiophenes were prepared in moderate to good yields with good functional-group tolerance.
Unusual behavior of the anionic species from (E)-1-chloro-3,3,3- trifluoropropene(HCFC-1233t)
Miyagawa, Akiko,Naka, Motoki,Yamazaki, Takashi,Kawasaki-Takasuka, Tomoko
supporting information; experimental part, p. 4395 - 4399 (2010/01/07)
(E)-1-Chloro-3,3,3-trifluoropropene was smoothly deprotonated by MeLi at the position β to the CF3 group, and exclusive formation of propargylic alcohols was observed by addition of appropriate carbonyl compounds as long as up to 1.6 equiv. of
