767607-36-3Relevant academic research and scientific papers
Isolable Pyridinium Trifluoromethoxide Salt for Nucleophilic Trifluoromethoxylation
Duran-Camacho, Geraldo,Ferguson, Devin M.,Kampf, Jeff W.,Bland, Douglas C.,Sanford, Melanie S.
supporting information, p. 5138 - 5142 (2021/07/19)
An isolable pyridinium trifluoromethoxide salt is prepared from the reaction of 4-dimethylaminopyridine with the commercially available liquid 2,4-dinitro(trifluoromethoxy)benzene. The salt is an effective trifluoromethoxide source for SN2 reactions to form trifluoromethyl ethers.
Direct Trifluoromethylation of Alcohols Using a Hypervalent Iodosulfoximine Reagent
Kalim, Jorna,Duhail, Thibaut,Pietrasiak, Ewa,Anselmi, Elsa,Magnier, Emmanuel,Togni, Antonio
supporting information, p. 2638 - 2642 (2021/01/21)
The direct trifluoromethylation of a variety of aliphatic alcohols using a hypervalent iodosulfoximine reagent afforded the corresponding ethers in moderate to good yields (14–72 %). Primary, secondary, and even tertiary alcohols, including examples derived from natural products, underwent this transformation in the presence of catalytic amounts of zinc bis(triflimide). Typical reaction conditions involved a neat mixture of 6.0 equivalents of the alcohol with 1.0 equivalent of the reagent, with the majority of reactions complete within 2 h with 2.5 mol % of the Lewis acid catalyst. Furthermore, experimental evidence was provided that the C?O bond-forming process occurred via the coordination of the alcohol to the iodine atom and subsequent reductive elimination.
Silver-Catalyzed Trifluoromethoxylation of Alkyl Trifluoroborates
Jiang, Xiaohuan,Tang, Pingping
supporting information, p. 5135 - 5139 (2020/07/04)
A silver-catalyzed trifluoromethoxylation of alkyl trifluoroborates with trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent has been reported for the first time. This reaction is performed under mild reaction conditions and has wide functional group compatibility. In addition, the mechanism of this site-specific trifluoromethoxylation is proposed as a radical pathway.
A deeper insight into direct trifluoromethoxylation with trifluoromethyl triflate
Marrec, Olivier,Billard, Thierry,Vors, Jean-Pierre,Pazenok, Sergii,Langlois, Bernard R.
experimental part, p. 200 - 207 (2010/04/30)
Commercially available fluorides (silver fluoride and n-tetrabutylammonium triphenyldifluorosilicate), combined with TFMT, allow a simple generation, in situ, of silver and n-tetrabutylammonium trifluoromethoxides which were able to react with electrophilic substrates. Silver trifluoromethoxide, which is usually more efficient than n-tetrabutylammonium trifluoromethoxide, converts, under mild conditions, primary aliphatic bromides and iodides, as well as primary and secondary benzylic or allylic bromides to the corresponding trifluoromethoxylated compounds. Several trifluoromethyl ethers, which could be valuable building-blocks, were prepared in such a way.
