31835-20-8Relevant articles and documents
Study of a Stable “Trifluoromethoxide Anion Solution” Arising from 2,4-Dinitro-Trifluoromethoxybenzene
Bonnefoy, Clémence,Chefdeville, Emmanuel,Panosian, Armen,Hanquet, Gilles,Leroux, Frédéric R.,Toulgoat, Fabien,Billard, Thierry
supporting information, p. 15986 - 15991 (2021/10/06)
Despite recent advances, trifluoromethoxylation remains a challenging reaction. Here we describe an efficient trifluoromethoxylative substitution, using an inexpensive and easy-to-handle reagent. By mixing DMAP with a slight excess of 1,4-dinitro-trifluoromethoxybenzene (DNTFB), a stable solution of trifluoromethoxide anion is obtained and can be used to perform a SN2 reaction without any silver additives. A precise study of the properties and behavior of this unusual stable solution of CF3O? species is also performed.
Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes
Hammond, Gerald B.,Kumon, Tatsuya,Lu, Zhichao,Umemoto, Teruo
supporting information, p. 16171 - 16177 (2021/06/27)
The trifluoromethoxy group has elicited much interest among drug and agrochemical discovery teams because of its unique properties. We developed trifluoromethyl nonafluorobutanesulfonate (nonaflate), TFNf, an easy-to-handle, bench-stable, reactive, and scalable trifluoromethoxylating reagent. TFNf is easily and safely prepared in a simple process in large scale and the nonaflyl part of TFNf can easily be recovered as nonaflyl fluoride after usage and recycled. The synthetic potency of TFNf was showcased with the underexplored synthesis of various trifluoromethoxylated alkenes, through a high regio- and stereoselective hydro(halo)trifluoromethoxylation of alkyne derivatives such as haloalkynes, alkynyl esters, and alkynyl sulfones. The synthetic merits of TFNf were further underscored with a high-yielding and smooth nucleophilic trifluoromethoxylation of alkyl triflates/bromides and primary/secondary alcohols.
Silver-Promoted Oxidative Benzylic C?H Trifluoromethoxylation
Yang, Haodong,Wang, Feng,Jiang, Xiaohuan,Zhou, Yu,Xu, Xiufang,Tang, Pingping
supporting information, p. 13266 - 13270 (2018/09/21)
A silver-promoted oxidative benzylic C?H trifluoromethoxylation has been reported for the first time. With trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent, various arenes, having diverse functional groups, undergo trifluoromethoxylation of their benzylic C?H bonds to form trifluoromethyl ethers under mild reaction conditions. In addition, the trifluoromethoxylation and the fluorination of methyl groups of electron-rich arenes have been achieved to prepare α-fluorobenzyl trifluoromethyl ethers in one step.