Superacid‐Catalyzed Trifluoromethylthiolation of Aromatic Amines

Milandou, Longin Justin Clair Bonazaba; Carreyre, Hélène; Alazet, Sébastien; Greco, Gino; Martin‐Mingot, Agnès; Loumpangou, Célestine Nkounkou; Ouamba, J. M.; Bouazza, Fodil; Billard, Thierry; Thibaudeau, Sébastien

doi:10.1002/anie.201609574

Cited by 64 publications

(23 citation statements)

References 62 publications

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“…The melting points were determined on OptiMelt MPA100. Products were characterized using 1 H, 13 C and 19 F NMR spectra, HRMS, elemental CHN analysis and melting points of solids. 1 H spectra were recorded on Bruker Avance 300 DPX, 1 H, 13 C and 19 F NMR spectra were recorded on Bruker Avance III 500 instruments, C, H, N analysis was recorded on Analizator Perkin-Elmer 2400 II, LC MS analysis was recorded on system Shimadzu LCMS-IT-TOF.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 , 25°C): δ = 7.41 (d, J = 8.5 Hz, 1 H, ArH), 6.65 (d, J = 8.6 Hz, 1 H, ArH) ppm. 13 (15).…”

Section: Decomposition Of Reagentmentioning

confidence: 99%

“…ArH) ppm 13. C NMR (126 MHz, CDCl 3 , 25°C): δ = 136.0, 132.8, 129.4 (q, J = 310 Hz),129.4, 123.4, 121.6, 119.3, 111.7, 95.4 ppm 19.…”

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confidence: 99%

“…Derivatives of trifluoromethanesulfenamide reagent were used for direct electrophilic trifluoromethylthiolation of activated aromatic and heteroaromatic molecules [10d,10e,12] and recently the second generation of reagent was used for the trifluoromethylthiolation of anilines in super acid media (SbF 5 ). [13] We were interested in the possibility of selective introduction of the trifluoromethylsulfanyl group on various aromatic com-Scheme 1. Modified Billard reagents.…”

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confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 , 25°C): δ = 7.17 (d, J = 2.0 Hz, 1 H, ArH), 7.14 (dd, J = 8.2, 2.0 Hz, 1 H, ArH), 6.90 (d, J = 8.2 Hz, 1 H, ArH) ppm. 13 C NMR (126 MHz, CDCl 3 , 25°C): δ = 146. 5, 143.7, 130.5, 129.6 (q, J = 308 Hz), 123.3, 116.0, 115.0 ppm.…”

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confidence: 99%

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Diversification of Trifluoromethylthiolation of Aromatic Molecules with Derivatives of Trifluoromethanesulfenamide

2018

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Trifluoromethylthiolation of aromatic compounds with different electrophilic reagents of the type ArNHSCF3 was studied in the presence of triflic acid as an activator. The effect of the reagent structure on the reactivity was studied with three different reagents: PhNHSCF3 (H/SCF3, 1a), 4‐ClC6H4NHSCF3 (Cl/SCF3, 1b) and C6F5NHSCF3 (F5/SCF3, 1c). p‐Chloro substituted reagent 1b was more stable than the unsubstituted 1a and was the most effective because it could not react by trifluoromethylthiolation of itself. This reaction was the most important side reaction of 1a. The pentafluoro derivative 1c was less reactive. Solvent played an important role in the transformation and, depending on the substrate, dichloromethane, hexane or trifluoroacetic acid gave the best yield of various trifluoromethylthiolated aromatic molecules (63–98 %).

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Section: Methodsmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 , 25°C): δ = 7.41 (d, J = 8.5 Hz, 1 H, ArH), 6.65 (d, J = 8.6 Hz, 1 H, ArH) ppm. 13 (15).…”

Section: Decomposition Of Reagentmentioning

confidence: 99%

“…ArH) ppm 13. C NMR (126 MHz, CDCl 3 , 25°C): δ = 136.0, 132.8, 129.4 (q, J = 310 Hz),129.4, 123.4, 121.6, 119.3, 111.7, 95.4 ppm 19.…”

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confidence: 99%

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confidence: 99%

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