60719-13-3Relevant academic research and scientific papers
Catalytic Asymmetric Homologation of 4-Substituted Cyclohexanones with CF3CHN2: Enantioselective Synthesis of α-Trifluoromethyl Cycloheptanones
Li, Shu-Sen,Sun, Shuo,Wang, Jianbo
supporting information, (2021/12/27)
Introduction of the trifluoromethyl group (CF3) into organic molecules in an enantioselective manner has attracted significant attention, but still remains a challenging problem. We herein report a catalytic asymmetric trifluoromethylation of cyclic ketones via a ScIII/chiral bisoxazoline-catalyzed homologation reaction by employing 2,2,2-trifluorodiazoethane (CF3CHN2) as the CF3 source. This desymmetrization process is highly efficient and generates two chiral centers with excellent diastereoselectivity and enantioselectivity, affording chiral α-trifluoromethyl cyclic ketones in a straightforward manner.
Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates
Vil’, Vera A.,Merkulova, Valentina M.,Ilovaisky, Alexey I.,Paveliev, Stanislav A.,Nikishin, Gennady I.,Terent’ev, Alexander O.
supporting information, p. 5107 - 5112 (2021/06/30)
The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.
Pd-catalyzed defluorination/arylation of α-trifluoromethyl ketones: Via consecutive β-F elimination and C-F bond activation
Xu, Lei,Zhang, Qi,Xie, Qiang,Huang, Bei,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 4406 - 4409 (2018/05/03)
An unprecedented Pd-catalyzed activation of a CF3 group is reported herein. The key to the success of this reaction is the combination of consecutive β-F elimination and C-F bond oxidative addition of a trifluoromethyl group. It also represents the first general application of α-trifluoromethyl ketones as building blocks by C-F bond activation.
Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones
Su, Xiaolong,Huang, Honggui,Yuan, Yaofeng,Li, Yi
, p. 1338 - 1341 (2017/01/24)
We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr
Synthesis of trifluoroethyl-substituted ketones from aldehydes and cyclohexanones
Morandi, Bill,Carreira, Erick M.
supporting information; experimental part, p. 9085 - 9088 (2011/10/13)
A trifluoromethylated symphony! A new transformation involving trifluoromethyl diazomethane generated in situ has been developed that allows direct access to trifluoroethyl ketone derivatives from aldehyde and cyclohexanone compounds (see scheme). Copyright
Dialkylzinc-aceelerated α-trifluoromethylation of carbonyl compounds catalyzed by late-transition-metal complexes
Tomita, Yuichi,Itoh, Yoshimitsu,Mikami, Koichi
scheme or table, p. 1080 - 1081 (2009/12/03)
Trifiuoromethylation of ketone silyl enol ethers is found to be significantly accelerated by late-transition-metal catalysts and dialkylzincs to give α-trifluoromethyl ketones in good yields. Addition of dialkylzinc is the key to the high yielding α-trifl
Radical trifluoromethylation of ketone silyl enol ethers by activation with dialkylzinc
Mikami, Koichi,Tomita, Yuichi,Ichikawa, Yoshiyuki,Amikura, Kazutoshi,Itoh, Yoshimitsu
, p. 4671 - 4673 (2007/10/03)
(Chemical Equation Presented) The radical trifluoromethylation of ketone silyl enol ethers gave α-CF3 ketones in good yields with wide scope of the ketonic substrates including acyclic ketones and cyclopentanone. The use of dialkylzinc to activ
Radical trifluoromethylation of ketone Li enolates
Itoh, Yoshimitsu,Mikami, Koichi
, p. 7199 - 7203 (2007/10/03)
It has generally been believed that highly basic Li enolates cannot be applied as substrates for radical trifluoromethylation due to defluorination of the α-CF3 product. However, Li enolates can be in fact employed for radical trifluoromethylat
Radical trifluoromethylation of Ti ate enolate: possible intervention of transformation of Ti(IV) to Ti(III) for radical termination
Itoh, Yoshimitsu,Mikami, Koichi
, p. 539 - 544 (2008/03/14)
The radical trifluoromethylation of ketone Ti ate enolates gave α-CF3 ketones in good yields. The use of excess amount of LDA and Ti(OiPr)4 in the preparation of Ti ate enolates is the key to the efficient radical trifluor
Radical trifluoromethylation of titanium ate enolate
Itoh, Yoshimitsu,Mikami, Koichi
, p. 649 - 651 (2007/10/03)
(Chemical Equation Presented) The radical trifluoromethylation of ketone titanium ate enolates gave α-CF3 ketones in good yields. The use of excess amount of LDA and Ti(OiPr)4 in the preparation of titanium ate enolates is
