Study of a Stable Trifluoromethoxide Anion Solution Arising from 2,4-Dinitro-Trifluoromethoxybenzene

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 S(N)2 reaction without any silver additives. A precise study of the properties and behavior of this unusual stable solution of CF3O- species is also performed.

Automated summary

Despite recent advances, trifluoromethoxylation is still a challenging reaction. This study presents an efficient trifluoromethoxylative substitution using an inexpensive and easy-to-handle reagent, which involves mixing DMAP with a slight excess of 1,4-dinitro-trifluoromethoxybenzene to obtain a stable solution of trifluoromethoxide anion for S(N)2 reaction without any silver additives. Detailed investigation on the properties and behavior of this stable CF3O- species is conducted.