pentafluoro-(4-iodophenyl)-lambda6-sulfane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaI (22.0 mg, 0.147 mmol) was added portion-wise to a solution of 1 (31.0 mg, 0.0974 mmol) and anisole (96.0 mg, 0.888 mmol) in CH3CN (53.5 mg). The reaction mixture was neutralized with Na2CO3 and filtered through Celite 545 using hexane. The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane afforded 25b (15.3 mg, 48%), 2-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (4.0 mg, 13%), 3-methoxy-4′-(pentafluorosulfanyl) biphenyl as a colorless oil (0.2 mg, 1%), a fraction containing both 3-methoxy-4′-(pentafluorosulfanyl)biphenyl and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl (1:1) as colorless oil (2.0 mg, 7%), and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (0.7 mg, 2%). filtered through Celite 545 The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (5.5 mg, 0.037 mmol) was added portion-wise to a solution of 1 (9.9 mg, 0.031 mmol) and p-xylene (60.1 mg, 0.566 mmol) in CH3CN (0.11 g). The reaction mixture was filtered through Celite 545 using CH2Cl2. The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane to afford 25b (1.4 mg, 14%) and 28b as a colorless oil (1.3 mg, 14%): MS (GC, EI): m/z=308 [M+], 181 [M+-SF5]. IR (ATR): {tilde over (v)}=2924, 1599, 1493, 1456, 1395, 1099, 833 cm−1. 1H NMR (500 MHz, CDCl3): δ=7.79 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 7.18 (d, J=8.3 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 7.02 (s, 1H), 2.36 (s, 3H), 2.22 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=155.0 (C), 145.6 (C), 139.5 (C), 132.0 (C), 130.5 (CH), 130.2 (CH), 129.4 (2CH), 128.8 (CH), 125.7 (2CH), 20.9 (CH3), 19.8 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.9 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm. The reaction mixture was filtered through Celite 545 The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (Bowden, et al., Tetrahedron 2000, 56, 3393-3408) Trimethylsilyl iodide (15.0 mg, 0.0750 mmol) was added to a solution of 1 (11.0 mg, 0.0346 mmol) in [BMIM][BF4] (67.6 mg). After stirring for 5 min the mixture was extracted with hexane (0.5 mL×3) and the combined extracts was evaporated to give pure 25b as a colorless oil (4.6 mg, 40%): MS (GC, EI): m/z=330 [M+], 311 [M+ F], 222, 96. 1H NMR (500 MHz, CDCl3): δ=7.82 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=137.9 (2CH), 127.5 (2CH), 98.2 (C) ppm. 19F NMR (470 MHz, CDCl3): δ=83.5 (quint, J=151 Hz, 1 F), 62.8 (d, J=151 Hz, 4 F) ppm. was extracted with hexane (0.5 mL×3) the combined extracts was evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaI (22.0 mg, 0.147 mmol) was added portion-wise to a solution of 1 (31.0 mg, 0.0974 mmol) and anisole (96.0 mg, 0.888 mmol) in CH3CN (53.5 mg). The reaction mixture was neutralized with Na2CO3 and filtered through Celite 545 using hexane. The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane afforded 25b (15.3 mg, 48%), 2-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (4.0 mg, 13%), 3-methoxy-4′-(pentafluorosulfanyl) biphenyl as a colorless oil (0.2 mg, 1%), a fraction containing both 3-methoxy-4′-(pentafluorosulfanyl)biphenyl and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl (1:1) as colorless oil (2.0 mg, 7%), and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (0.7 mg, 2%). filtered through Celite 545 The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (5.5 mg, 0.037 mmol) was added portion-wise to a solution of 1 (9.9 mg, 0.031 mmol) and p-xylene (60.1 mg, 0.566 mmol) in CH3CN (0.11 g). The reaction mixture was filtered through Celite 545 using CH2Cl2. The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane to afford 25b (1.4 mg, 14%) and 28b as a colorless oil (1.3 mg, 14%): MS (GC, EI): m/z=308 [M+], 181 [M+-SF5]. IR (ATR): {tilde over (v)}=2924, 1599, 1493, 1456, 1395, 1099, 833 cm−1. 1H NMR (500 MHz, CDCl3): δ=7.79 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 7.18 (d, J=8.3 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 7.02 (s, 1H), 2.36 (s, 3H), 2.22 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=155.0 (C), 145.6 (C), 139.5 (C), 132.0 (C), 130.5 (CH), 130.2 (CH), 129.4 (2CH), 128.8 (CH), 125.7 (2CH), 20.9 (CH3), 19.8 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.9 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm. The reaction mixture was filtered through Celite 545 The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (5.5 mg, 0.037 mmol) was added portion-wise to a solution of 1 (9.9 mg, 0.031 mmol) and p-xylene (60.1 mg, 0.566 mmol) in CH3CN (0.11 g). The reaction mixture was filtered through Celite 545 using CH2Cl2. The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane to afford 25b (1.4 mg, 14%) and 28b as a colorless oil (1.3 mg, 14%): MS (GC, EI): m/z=308 [M+], 181 [M+-SF5]. IR (ATR): {tilde over (v)}=2924, 1599, 1493, 1456, 1395, 1099, 833 cm−1. 1H NMR (500 MHz, CDCl3): δ=7.79 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 7.18 (d, J=8.3 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 7.02 (s, 1H), 2.36 (s, 3H), 2.22 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=155.0 (C), 145.6 (C), 139.5 (C), 132.0 (C), 130.5 (CH), 130.2 (CH), 129.4 (2CH), 128.8 (CH), 125.7 (2CH), 20.9 (CH3), 19.8 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.9 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm. The reaction mixture was filtered through Celite 545 The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (Bowden, et al., Tetrahedron 2000, 56, 3393-3408) Trimethylsilyl iodide (15.0 mg, 0.0750 mmol) was added to a solution of 1 (11.0 mg, 0.0346 mmol) in [BMIM][BF4] (67.6 mg). After stifling for 5 min the mixture was extracted with hexane (0.5 mL×3) and the combined extracts was evaporated to give pure 25b as a colorless oil (4.6 mg, 40%): MS (GC, EI): m/z=330 [M+], 311 [M+ F], 222, 96. 1H NMR (500 MHz, CDCl3): δ=7.82 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=137.9 (2CH), 127.5 (2CH), 98.2 (C) ppm. 19F NMR (470 MHz, CDCl3): δ=83.5 (quint, J=151 Hz, 1 F), 62.8 (d, J=151 Hz, 4 F) ppm. the mixture was extracted with hexane (0.5 mL×3) the combined extracts was evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Obtained by starting from (S)-5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 1-iodo-4-pentafluorosulfanyl-benzene. A 1.3 M solution of isopropylmagnesium chloride-lithium chloride-complex in tetrahydrofurane is used instead of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane. Obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde and 1-iodo-4-pentafluorosulfanyl-benzene. A 1.3 M solution of isopropylmagnesium chloride-lithium chloride-complex in tetrahydrofurane is used instead of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane. Obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(pentafluorothio)aniline (15.0 g, 68.4 mmol) and ice (40.0 g) in hydrochloric acid (12M, 30 ml) was added a solution of sodium nitrite (5.0 g, 72.5 mmol) in water (120 ml) at 0° C. After stirring for 2 min, the mixture was added to potassium iodide (13.0 g, 78.3 mmol) in water (120 ml), ensuring the temperature did not rise above 10° C. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature for 60 h. The mixture was extracted with diethyl ether (2×100 ml) and the combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica, 300 g), eluting with diethyl ether:cyclohexane [1:10]. The appropriate fractions were combined and concentrated to give the title compound (16.6 g). did not rise above 10° C The reaction mixture was stirred at 0° C. for 10 min at room temperature for 60 h The mixture was extracted with diethyl ether (2×100 ml) the combined extracts were washed with brine dried (MgSO4) concentrated in vacuo The residue was purified by column chromatography (silica, 300 g) eluting with diethyl ether concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(pentafluorothio)aniline (15.0 g, 68.4 mmol) and ice (40.0 g) in hydrochloric acid (12M, 30 ml) was added a solution of sodium nitrite (5.0 g, 72.5 mmol) in water (120 ml) at 0° C. After stirring for 2 min, the mixture was added to potassium iodide (13.0 g, 78.3 mmol) in water (120 ml), ensuring the temperature did not rise above 10° C. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature for 60 h. The mixture was extracted with diethyl ether (2×100 ml) and the combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica, 300 g), eluting with diethyl ether/cyclohexane [1:10]. The appropriate fractions were combined and concentrated to give the title compound (16.6 g). did not rise above 10° C The reaction mixture was stirred at 0° C. for 10 min at room temperature for 60 h The mixture was extracted with diethyl ether (2×100 ml) the combined extracts were washed with brine dried (MgSO4) concentrated in vacuo The residue was purified by column chromatography (silica, 300 g) eluting with diethyl ether/cyclohexane [1:10] concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaI (22.0 mg, 0.147 mmol) was added portion-wise to a solution of 1 (31.0 mg, 0.0974 mmol) and anisole (96.0 mg, 0.888 mmol) in CH3CN (53.5 mg). The reaction mixture was neutralized with Na2CO3 and filtered through Celite 545 using hexane. The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane afforded 25b (15.3 mg, 48%), 2-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (4.0 mg, 13%), 3-methoxy-4′-(pentafluorosulfanyl) biphenyl as a colorless oil (0.2 mg, 1%), a fraction containing both 3-methoxy-4′-(pentafluorosulfanyl)biphenyl and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl (1:1) as colorless oil (2.0 mg, 7%), and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (0.7 mg, 2%). filtered through Celite 545 The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane