587885-96-9Relevant articles and documents
Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2·bpy
Pan, Shitao,Wang, Xiu,Ni, Chuanfa,Hu, Jinbo
, (2021/10/12)
(Trifluoromethyl)zinc complexes have been widely used in metal-mediated trifluoromethylation reactions. However, direct nucleophilic addition with a (trifluoromethyl)zinc complex is rare. In this article, we describe an unprecedented trifluoromethylation of azinium salts using Zn(CF3)2·bpy as CF3 source, giving 1-(4-methoxybenzyl)-2-(trifluoromethyl)-1,2-dihydroquinolines as products. The latter species were further transformed to 2-trifluoromethylquinolines under oxidative conditions. This work also shows that ligands play an important role in tuning the reactivity of (trifluoromethyl)zinc complexes.
Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones
Marull, Marc,Schlosser, Manfred
, p. 1576 - 1588 (2007/10/03)
The acid-catalyzed cyclization-condensation between anilines and ethyl 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones (1), which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. These undergo halogen/metal exchange, generating 2-trifluoromethyl-4-quinolyllithiums, when treated with butyllithium, and hydrogen/metal exchange, generating 4-bromo-2-trifluoromethyl-3-quinolyllithiums, when treated with lithium diisopropylamide. Trapping of the latter intermediates provides 3-functionalized products that may be further elaborated by electrophilic substitution of the bromine atom. A few unexpected findings resulted from these investigations, the most noteworthy being an unprecedented buttressing effect and a counterintuitive halogen reactivity. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).