204708-09-8Relevant academic research and scientific papers
Direct Synthesis of Tri-/Difluoromethyl Ketones from Carboxylic Acids by Cross-Coupling with Acyloxyphosphonium Ions
Ispizua-Rodriguez, Xanath,Munoz, Socrates B.,Krishnamurti, Vinayak,Mathew, Thomas,Prakash
supporting information, p. 15908 - 15913 (2021/10/07)
A simple and straightforward approach to the synthesis of trifluoromethyl and difluoromethyl ketones from widely available carboxylic acids is disclosed. The transformation utilizes an acyloxyphosphonium ion as the active electrophile, conveniently generated in situ from the carboxylic acid substrate by using commodity chemicals. The utility of the reaction system is exemplified by its chemoselectivity, with tolerance to a variety of important functional groups. The late-stage functionalization of carboxylic acid active pharmaceutical ingredients and pharmaceutically relevant compounds is also discussed.
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes - A Short Synthesis of Celebrex (Celecoxib)
Sommer, Heiko,Braun, Max,Schr?der, Benjamin,Kirschning, Andreas
supporting information, p. 121 - 125 (2017/10/07)
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex (celecoxib).
An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds
Wang, Yongdong,Han, Jing,Chen, Jie,Cao, Weiguo
, p. 8256 - 8262 (2015/10/05)
A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560.
Highly efficient asymmetric epoxidation of electron-deficient α,β-enones and related applications to organic synthesis
Zheng, Changwu,Li, Yawen,Yang, Yingquan,Wang, Haifeng,Cui, Haifeng,Zhang, Junkang,Zhao, Gang
supporting information; experimental part, p. 1685 - 1691 (2011/02/25)
The asymmetric epoxidation of electrondeficient olefins has been achieved using inexpensive and readily available prolinols as catalysts with good to excellent yields and enantioselectivities. The utility of the resulting chiral epoxides was illustrated b
Reaction of 1,2-unsaturated trifluoromethyl ketones and their conversion to 1-(trifluoromethyl)furan derivatives
Zhang, Dehui,Yuan, Chengye
, p. 3916 - 3924 (2008/02/13)
A novel synthetic approach leading to 1-(trifluoromethyl)furan derivatives is reported. 4-Aryl-1,1,1-trifluorobut-3-en-2-one was iodinated and subsequently reduced to give the corresponding alcohol. The resultant iodo compound was then subjected to coupli
First synthesis of a α-trifluoromethyl allenol ether via the Julia-Lythgoe process
Yoshimatsu,Hibino
, p. 1395 - 1398 (2007/10/03)
α-Trifluoromethyl allenol ethers 9a - e were prepared in moderate to good yields hy the Julia-Lythgoe process using β-ethoxy-β-trifluoromethyl vinylic sulfone 3. Several reactions of 9c were examined to give α,β-unsaturated trifluoromethyl ketone derivatives 11 and 12.
A convenient one-pot synthesis of 6-trifluoromethyl-pyridines
Katsuyama, Isamu,Ogawa, Seiya,Nakamura, Hiroko,Yamaguchi, Yoshihiro,Funabiki, Kazumasa,Matsui, Masaki,Muramatsu, Hiroshige,Shibata, Katsuyoshi
, p. 779 - 785 (2007/10/03)
α,β-Unsaturated trifluoromethyl ketones (1) react with primary enamines (2) such as β-aminocrotononitrile and β-aminocrotonates in the presence of phosphorus oxychloride / pyridine adsorbed on silica gel and manganese dioxide, providing good to high yield
