Trifluoro methylation

Trifluoperazine dihydrochloride (10-[3- 4-methyl-l-piperazinyl propyl]-2-trifluoro-methyl-phenothiazine 2HCI) [440-17-5] M 480.4, m 240-243 , 242-243 , pK, 3.9, pKj 8.1. 

Sulfonates react with a variety of nucleophiles. Synthesis of M A -bis(trifluoro-methyl)aminotnfluoromethanesulfonate and its reactions with nucleophiles were investigated [33] (equation 31) (Table 13). Nucleophilic attack occurs at either nitrogen or sulfur amines give complex mixtures [33]. Polyfluoroalkyl fluorosul-fates react with amines, alcohols, or alkoxides to yield polyfluoroalkyl sulfamates and dialkyl sulfates, respectively [34] (equation 32) (Table 13). In these reactions. 

Although iodides are more reactive than bromides, 2-(trifluoro-methyl)pyridine was obtained in 95% yield from 2-bromopyridine and CF3Br using an undivided electrochemical cell, DMF, and a sacrificial copper anode. CF3Cu was the reactive intermediate (92CC53). Photochem-... 

Trifluoroacetonitrile oxide has been used in the synthesis of trifluoro-methyl isoxazoles and isoxazolines (84BCJ2184 86BCJ2631). In the presence of a base it dimerizes to a dioxadiazine (84JOC919). 

Aniline, 2-biomo [Benzenamine, 2-bromo-], p-biomination of, 55, 23 Aniline, 3-biomo- [Benzenamine, 3 biomo-], p-biomination of, 55, 23 ANILINE, 4-bromo-/V,A -dimethyl-3-(tn-fluoromethyl)- [Benzenamine, 4-bromo-A,eAr-dimethyl-3-(trifluoro-methyl-], 55, 20... 

A,A-Dibenzyl-2-(ethoxycarbonylmethyl)amino-4-(trifluoromethyl)aniline (27) underwent reductive debenzylation and spontaneous cyclization to 6-trifluoro-methyl-3,4-dihydro-2(17/)-quinoxalinone (28) [Pd(OH)2/C, EtOH, H2 (3 atm), 3 days 97%]. " °... 

As most readers will undoubtedly be aware, the study of trifluoro-methyl organometallic compounds, and the initiation of this area as a field of research, began with the discovery of bis(trifluoromethyl)mer-cury by Emele us and Haszeldine (1) in 1949 and continued with their associated research programs. Since that time, a steady, and sometimes spectacular, international research effort has continued over the past twenty-five years that has involved many laboratories (2). 

The formation of ethers such as 1806 by EtsSiH 84b can also be catalyzed by trityl perchlorate to convert, e.g., benzaldehyde in 84% yield into dibenzyl ether 1817 [48]. The combination of methyl phenethyl ketone 1813 with O-silylated 3-phenyl-n-pro-panol 1818, in the presence of trityl perchlorate, leads to the mixed ether 1819 in 68% yield [48] (Scheme 12.15). Instead of trityl perchlorate, the combination of trityl chloride with MesSiH 84a or EtsSiH 84b and sodium tetrakis[3,5-bis-(trifluoro-methyl)phenyl]borane as catalyst reduces carbonyl groups to ethers or olefins [49]. Employing TMSOTf 20 as catalyst gives very high yields of ethers. Thus benzaldehyde reacts with O-silylated allyl alcohol or O-silylated cyclohexanol to give the... 

Figure 6 Structure of PD81,723, (2-amino-4,5-dimethyl-trienyl)[3-(trifluoro-methyl) phenyl]methanone and adenosine At agonists/antagonists.

Tagat, J.R., Steensma, R.W., McCombie, S.W. et al. (2001) Piperazine-based CCR5 antagonists as HIV-1 inhibitors. II. Discovery of 1 - [(2,4-dimethyl-3-pyridinyl)carbonyl]-4- methyl-4- [3 (S)-methyl-4- [ 1 (5)- [4-(trifluoro- methyl)phenyl]ethyl]-l-piperazinyl]-piperidine Nl-oxide (sch-350634), an orally bioavailable, potent CCR5 antagonist. Journal of Medicinal Chemistry, 44 (21), 3343-3346. 

Shreier et al. [77] developed an HPLC method for the determination of Bayluscide residues in muscle fillet tissues of fish exposed to Bayluscide and 3-(trifluoro-methyl)-4-nitrophenol during sea lamprey control treatments in the Great Lakes (USA). 

Some decomposition occurs during the reduction free nickel ion is present in the filtrate, and some free bis(trifluoro-methyl)-l,2-dithiete is produced which is removed by the pentane washes. 

Bromoanlsole Anisole, o-bromo- (8) Benzene, 1-bromo-2-methoxy- (9) (578-57-4) Methyl trifluoromethanesulfonate Methanesulfonic add, trifluoro-, methyl ester (8,9) (333-27-7)... 

Several comparative studies are available in the literature, which clearly shows that, according to the latest results, tetrafluoro-pheny/ azides (AZ), trifluoro-methyl-phenyl diazirines (DZR), and particularly benzophenone (BP) are the best choice (Scheme 3.). Diazocarbonyl compounds, which played a historically role in the evolution of PAL, can also be considered together with aryl-diazonium salts [6] (not shown). For aryl azides the more common unsubstituted photophore is presented. It should be noted that tetrafluoro-phenyl azides have an increased reactivity towards CH-groups and they do not rearrange. Other substituted phenyl azides can readily alter the excitation wavelength allowing the application of milder or differential photoactivation. 

The quaternary ammonium salt 48 derived from (+)-ephedrine was utilized for the enantioselective addition of diethyl zinc to aldehydes.1421 The chiral ammonium fluorides 7 (R=4-CF3 or 2,4-(CF3)2, X=F) were also useful for the enantioselective trifluoro-methylation of aldehydes and ketones with moderate enantioselectivity,1431 shown in Scheme 17... 

K. Iseki, T. Nagai, Y. Kobayashi, Asymmetric Trifluoro-methylation of Aldehydes and Ketones with Trifluoro-methyltrimethylsilane Catalyzed by Chiral Quaternary Ammonium Fluorides , Tetrahedron Lett. 1994, 35, 3137-3138. 

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