Compound characterization data — Kuchukulla et al., 2026

Ratnakar Reddy Kuchukulla, Daiki Harano, Norio Shibata. “Oxidative ArylSF₄-tetrafluoroethylation to N-hydroxydicarboximides via in situ generated silver intermediate from silver(I) fluoride.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007883/v1

2i
TLC (hexane/ethyl acetate 1:3)	Rf = 0.3
Melting point	124.5–125.3 °C
¹H NMR (700 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 8.21 (d, J = 7.5 Hz, 1H), 8.16 (s, 1H), 8.04 (d, J = 7.7 Hz, 1H)
¹³C NMR (126 MHz, DMSO-d₆)	δ 163.0, 162.8, 133.9 (q, J = 32.7 Hz), 132.5, 131.6 (q, J = 4.1 Hz), 130.0, 124.3, 123.9, 119.7 (q, J = 3.8 Hz)
¹⁹F NMR (658 MHz, DMSO-z₆)	δ −61.07
HRMS (ESI)	m/z: [M−H]⁻ calculated for C₉H₃NO₃F₃ 230.0065; found: 230.0065
IR (KBr)	3267, 1728, 1502, 1432, 1320, 1136, 914, 863, 694, 555 cm⁻¹

1-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)pyrrolidine-2,5-dione
Identifier	3a
Melting point	122–123 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.84 (dt, J = 2.6, 0.9 Hz, 1H), 8.16 (dd, J = 8.5, 2.3 Hz, 1H), 7.93 (d, J = 8.6 Hz, 1H), 2.84 (s, 4H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 169.0–168.3 (m), 168.2, 145.3, 136.3, 129.7, 129.6 (q, J = 33.9 Hz), 129.5, 122.47 (q, J = 273.5 Hz), 25.56
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 43.53–34.21 (m), −62.47, −74.22–−78.25 (m), −105.21 (ddt, J = 13.3, 9.6, 3.8 Hz)
HRMS (ESI)	[M+H]⁺: calculated for C₁₂H₈F₁₁N₂O₃S: 469.0080, found 469.0091
IR (KBr)	2925, 1766, 1332, 1142, 1079, 807

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3b
Melting point	160–161 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.85 (dt, J = 2.6, 0.9 Hz, 1H), 8.17 (dd, J = 8.5, 2.3 Hz, 1H), 7.96 (d, J = 8.5 Hz, 1H), 7.92 (dd, J = 5.5, 3.1 Hz, 2H), 7.83 (dd, J = 5.5, 3.1 Hz, 2H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ δ 168.8 (p, J = 27.5 Hz), 161.9, 145.4, 136.3, 135.4, 129.6 (q, J = 33.7 Hz), 128.9, 124.4, 122.5 (q, J = 273.4 Hz), 121.8
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.55–40.41 (m), −62.48, −76.02–−76.11 (m), −104.48–−104.54 (m)
HRMS (ESI)	[M+H]⁺: calculated for C₁₆H₈F₁₁N₂O₃S: 517.0080, found 517.0087
IR (KBr)	1758, 1329, 1075, 810, 732 cm⁻¹

5-nitro-2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3c
Melting point	165–166 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.86 (dt, J = 2.4, 0.8 Hz, 1H), 8.75 (dd, J = 2.0, 0.6 Hz, 1H), 8.70 (dd, J = 8.2, 2.0 Hz, 1H), 8.19 (dd, J = 8.5, 2.3 Hz, 1H), 8.15 (dd, J = 8.2, 0.6 Hz, 1H), 7.96 (d, J = 8.5 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 159.4, 152.4, 145.4, 136.4, 133.1, 130.4, 130.2, 130.0–129.5 (m), 125.9, 121.8, 119.9
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.82–40.54 (m), −62.46, −76.11, −104.85–−105.09 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₆H₆F₁₁N₃NaO₅S: 583.9750, found 583.9753
IR (KBr)	1763, 1536, 1336, 1203, 1064, 794

4,5,6,7-tetrachloro-2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3d
Melting point	163–164 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.85 (d, J = 2.3 Hz, 1H), 8.18 (dd, J = 8.6, 2.3 Hz, 1H), 7.95 (d, J = 8.5 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 170.2–166.9 (m), 157.6, 145.4, 141.8, 141.1, 136.4, 130.9, 130.5, 129.7 (q, J = 33.4 Hz), 129.8, 129.6, 124.6, 122.4 (q, J = 273.4 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.63 (p, J = 9.4 Hz), −62.47 (d, J = 5.0 Hz), −76.15, −105.26
HRMS (ESI)	[M+Na]⁺: calculated for C₁₆H₃Cl₄F₁₁N₂NaO₃S: 674.8341, found 674.8336
IR (KBr)	1770, 1326, 1200, 1079, 817, 732 cm⁻¹

5-methyl-2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3e
Melting point	134–135 °C
¹H NMR (500 MHz, CDCl₃)	δ 8.90–8.84 (m, 1H), 8.18 (dd, J = 8.6, 2.4 Hz, 1H), 7.98 (d, J = 8.6 Hz, 1H), 7.81 (d, J = 7.6 Hz, 1H), 7.73 (dt, J = 1.5, 0.8 Hz, 1H), 7.63 (ddd, J = 7.7, 1.5, 0.8 Hz, 1H), 2.55 (s, 3H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 169.3–168.5 (m), 162.2, 162.0, 145.3, 136.3, 136.0, 129.6, 129.4, 129.2, 129.2, 126.2, 124.8, 124.4, 121.8, 22.3
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.45 (dt, J = 20.6, 10.2 Hz), −62.46, −76.04, −104.37–−104.51 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₇H₉F₁₁N₂NaO₃S: 553.0056, found 553.0068
IR (KBr)	1756, 1333, 1235, 1146, 809, 733 cm⁻¹

5-methoxy-2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3f
Melting point	136–137 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.85 (d, J = 2.3 Hz, 1H), 8.17 (dd, J = 8.7, 2.3 Hz, 1H), 7.96 (d, J = 8.6 Hz, 1H), 7.82 (d, J = 8.4 Hz, 1H), 7.36 (d, J = 2.4 Hz, 1H), 7.26 (dd, J = 8.4, 2.4 Hz, 1H), 3.95 (s, 3H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 170.7–168.0 (m), 165.6, 162.2, 161.8, 145.3, 136.3, 131.4, 129.6, 129.4, 126.4, 123.2, 121.8, 121.5, 120.7, 108.8, 56.3
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.63–40.31 (m), −62.45, −76.02, −104.19–−104.48 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₇H₉F₁₁N₂NaO₄S: 569.0005, found 569.0012
IR (KBr)	2921, 1755, 1331, 1235, 1147, 810, 734 cm⁻¹

N-acetyl-N-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)acetamide
Identifier	3g
Melting point	110–111 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.85 (dt, J = 2.4, 0.8 Hz, 1H), 8.18 (dd, J = 8.5, 2.3 Hz, 1H), 7.92 (d, J = 8.5 Hz, 1H), 2.47 (s, 6H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 171.9, 169.4–168.3 (m), 145.4, 136.4, 130.2–129.2 (m), 123.2, 121.6, 29.7, 24.6 (d, J = 108.2 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 41.26 (p, J = 11.6 Hz), −62.47, −74.23 (tt, J = 11.0, 6.1 Hz), −102.39–−102.47 (m)
HRMS (ESI)	[M+H]⁺: calculated for C₁₂H₉F₁₁N₂NaO₃S: 493.0056, found 493.0056
IR (KBr)	1752, 1600, 1331, 1181, 808 cm⁻¹

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)-1H-benzo[de]isoquinoline-1,3(2H)-dione
Identifier	3h
Melting point	150–151 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.88–8.85 (m, 1H), 8.65 (d, J = 7.3 Hz, 2H), 8.29 (dd, J = 8.2, 1.1 Hz, 2H), 8.18 (d, J = 2.3 Hz, 1H), 8.01 (d, J = 8.5 Hz, 1H), 7.81 (t, J = 7.7 Hz, 2H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 160.9, 145.3, 136.3, 135.1, 132.2, 131.9, 129.6, 129.4, 127.6, 127.3, 123.3, 122.7, 121.8, 121.7
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 41.09 (p, J = 10.9 Hz), −62.43, −75.33–−75.43 (m), −103.57–−106.52 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₇H₉F₁₁N₂NaO₄S: 589.0067, found 589.0056
IR (KBr)	2963, 1722, 1678, 13329, 1233, 1172, 806, 735 cm⁻¹

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-(trifluoromethyl)pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)-5-(trifluoromethyl)isoindoline-1,3-dione
Identifier	3i
Melting point	140–141 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.86 (dt, J = 2.6, 0.9 Hz, 1H), 8.21–8.15 (m, 2H), 8.13–8.07 (m, 2H), 7.96 (d, J = 8.5 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 169.1–168.3 (m), 160.4, 160.3, 145.4, 137.4 (q, J = 34.1 Hz), 136.4, 133.0, 132.4 (d, J = 4.1 Hz), 131.6, 129.7 (q, J = 33.8 Hz), 129.5, 125.1, 123.3 (d, J = 45.1 Hz), 121.9, 121.8, 121.7 (d, J = 3.7 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.69–40.54 (m), −62.48, −63.12, −76.11, −102.30–−106.71 (m)
HRMS (ESI)	[M+H]⁺: calculated for C₁₇H₇F₁₄N₂O₃S: 584.9954, found 584.9955
IR (KBr)	1768, 1328, 1143, 1077, 907, 808 cm⁻¹

2-(1-((4-chlorophenyl)tetrafluoro-λ⁶-sulfaneyl)-1,2,2,2-tetrafluoroethoxy)isoindoline-1,3-dione
Identifier	3j
Melting point	110–111 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 7.94–7.90 (m, 2H), 7.84–7.81 (m, 2H), 7.77–7.72 (m, 2H), 7.42 (d, J = 8.6 Hz, 2H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 161.9, 161.8, 154.1 (p, J = 18.9 Hz), 137.5, 135.3, 135.3, 128.9, 128.8, 128.7, 127.5 (t, J = 5.0 Hz), 124.4, 118.6 (dd, J = 288.8, 34.7 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 51.06 (dt, J = 20.7, 10.1 Hz), −76.01–−76.12 (m), −104.14–−104.27 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₆H₈ClF₈NNaO₃S: 503.9683, found 503.9681
IR (KBr)	1758, 1476, 1308, 1209, 1069, 781, 673 cm⁻¹

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(2-fluorophenyl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3k
Melting point	116–117 °C
¹H NMR (500 MHz, CDCl₃)	δ 7.93 (dd, J = 5.5, 3.1 Hz, 2H), 7.87–7.81 (m, 3H), 7.50 (tdd, J = 8.5, 4.4, 1.6 Hz, 1H), 7.26–7.18 (m, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 161.9, 156.8, 154.7, 141.9, 135.3, 133.3 (d, J = 9.2 Hz), 128.7 (d, J = 25.1 Hz), 124.3, 123.8, 117.9 (d, J = 23.8 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 55.13 (ddd, J = 23.4, 13.2, 9.7 Hz), −76.08, −104.70–−104.86 (m), −107.08–−107.27 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₆H₈F₉NNaO₃S: 487.9979, found 487.9968
IR (KBr)	1760, 1487, 1226, 816, 727 cm⁻¹

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(4-nitrophenyl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3l
Melting point	138–139 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.34–8.29 (m, 1H), 8.01 (d, J = 9.2 Hz, 1H), 7.93 (dd, J = 5.5, 3.0 Hz, 1H), 7.84 (dd, J = 5.5, 3.1 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 167.8, 161.9, 159.7 (p, J = 21.8 Hz), 148.9, 135.5, 134.4, 132.7, 128.8, 127.8–127.2 (m), 124.4, 124.0, 123.6, 118.5 (dd, J = 289.2, 32.2 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 50.60–50.41 (m), −76.07 (t, J = 10.4 Hz), −104.20 (tt, J = 16.3, 8.1 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₆H₈F₈N₂NaO₅S: 514.9924, found 514.9924
IR (KBr)	1808, 1756, 1534, 1468, 1361, 753 cm⁻¹

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(5-nitropyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3m
Melting point	175–176 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 9.43–9.36 (m, 1H), 8.70 (dd, J = 8.8, 2.6 Hz, 1H), 8.09–8.03 (m, 1H), 7.95–7.90 (m, 2H), 7.87–7.80 (m, 2H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 169.9–168.8 (m), 161.9, 145.2, 143.7, 135.5, 134.4, 134.1, 128.9, 124.4, 124.4, 123.7, 122.5
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 41.31–40.99 (m), −76.05, −104.38–−104.68 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₅H₇F₈N₃NaO₅S: 515.9876, found 515.9871
IR (KBr)	1756, 1451, 979, 609
IR (KBr)	1805, 1752, 1532, 1358, 1190, 979 cm⁻¹

2-(1,2,2,2-tetrafluoro-1-(tetrafluoro(pyridin-2-yl)-λ⁶-sulfaneyl)ethoxy)isoindoline-1,3-dione
Identifier	3n
Melting point	125–126 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.58 (ddd, J = 4.7, 1.9, 0.8 Hz, 1H), 7.94–7.88 (m, 3H), 7.84–7.79 (m, 3H), 7.48 (ddd, J = 7.5, 4.7, 0.9 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 167.3–166.7 (m), 161.9, 148.0, 138.8, 135.3, 128.9, 126.7, 124.3, 121.6
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 40.14 (dq, J = 13.7, 10.2 Hz), −75.98–−76.08 (m), −104.53 (ddt, J = 13.3, 9.0, 3.8 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₅H₈F₈N₂NaO₃S: 471.0026, found 471.0025
IR (KBr)	1758, 1225, 1194, 1067, 808, 658 cm⁻¹

2-(1-((5-bromopyridin-2-yl)tetrafluoro-λ⁶-sulfaneyl)-1,2,2,2-tetrafluoroethoxy)isoindoline-1,3-dione
Identifier	3o
Melting point	97–98 °C
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.60 (dd, J = 2.4, 0.7 Hz, 1H), 8.02 (dd, J = 8.7, 2.4 Hz, 1H), 7.90 (dd, J = 5.5, 3.1 Hz, 2H), 7.82 (dd, J = 5.5, 3.0 Hz, 2H), 7.70 (dd, J = 8.6, 0.7 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 165.3 (p, J = 22.7 Hz), 161.9, 148.9, 141.2, 128.9, 124.4, 123.8, 122.8, 119.4 (td, J = 291.2, 32.8 Hz)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 41.31–41.23 (m), −75.95–−76.14 (m), −103.79–−105.60 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₅H₇F₈BrN₂NaO₃S: 548.9131, found 548.9133
IR (KBr)	1809, 1761, 1450, 1361, 980, 872 cm⁻¹

4
¹H NMR (700 MHz, CHLOROFORM-D)	δ 8.84 (dt, J = 2.4, 0.8 Hz, 1H), 8.23–8.13 (m, 1H), 7.92 (d, J = 8.5 Hz, 1H), 5.74 (ddq, J = 43.1, 10.1, 5.0 Hz, 1H)
¹³C NMR (176 MHz, CHLOROFORM-D)	δ 169.7–169.0 (m), 145.2, 136.3, 129.5 (q, J = 34.1 Hz), 123.2, 122.1, 121.8–121.5 (m), 107.3–104.9 (m)
¹⁹F NMR (658 MHz, CHLOROFORM-D)	δ 44.34 (qd, J = 10.3, 4.8 Hz), −62.46, −74.76 (qt, J = 15.4, 7.8 Hz), −166.23 (dq, J = 43.1, 9.4 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₄F₁₁NNaS: 377.9786, found 377.9786
IR (KBr)	2929, 817, 713 661 cm⁻¹

Compounds 3a–3o and 4
¹H, ¹³C and ¹⁹F NMR spectra	Image data were not transcribed
HSQC spectrum of 3a	Image data were not transcribed