Phosphorous compounds trifluoromethyl

A trifluoromethyl group bound directly to phosphorous is deshielded slightly more than the respective nitrogen compound (Scheme 5.18). 

Majority of known perfluoroalkylated aromatic heterocyclic compounds contain one or several nitrogen atom(s) in the aromatic ring. Examples of fluoroalkylated aromatic six-membered heterocycles containing atoms, such as phosphorous or antimony are extremely rare and this is the reason why this chapter is mostly limited to preparation and chemical transformations of nitrogen-cotitammg aromatic heterocycles, providing limited number of references to only few known examples of trifluoromethyl s-1,3,5,2,4,6-triazatriphosphinines. 

The same method was also used for the synthesis of the anti-malarial compound mefloquine. Heterocyclization of 2-trifluoromethylaniline with trifluoroacetic acid ethyl ester provides 2,8-6w-(trifluoromethyl)-4-hydroxyquinoline. Bromination with phosphorous tribromide, followed a carbon monoxide introduction, affords 2,7-trifluoromethyl-4-carboxylic acid quinoline. Amide formation and pyridine reduction completes the synthesis providing mefloquine in high yields. ... 

An enantioselective, organocatalytic domino Friedel-Crafts aminoalkylation with imines generated in situ from trifluoroacetaldehyde hemiacetal (219) and aniline 220 for the synthesis of chiral trifluoromethyl-containing compounds was reported by Ma and coworkers (Scheme 42.51). Very high activity and selectivity was obtained using chiral phosphoric acid catalysts [109]. 

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