The Journal of Organic Chemistry
Note
equiv of DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248
mg), isolation method B: yellow solid (310 mg, 86%). 1H NMR (500
MHz, CDCl3): δ 7.73−7.77 (m, 2H), 7.68−7.73 (m, 2H), 3.32 (s,
3H). 13C{1H} NMR (126 MHz, CDCl3): δ 139.1, 133.1, 130.0, 129.2,
42.9. IR (neat): 3074, 3017, 2920, 1566, 1466, 1404, 1200, 1085,
1062, 1017, 975, 953, 824, 758, 715 cm−1. HRMS (ESI-TOF) m/z:
[M + H]+ Calcd for C7H7BrINOS 359.8549; Found 359.8559. Mp =
95.9−96.8 °C.
N-Iodo-S-(4-cyanophenyl)-S-methyl Sulfoximine (2m). 1m (1
mmol, 149 mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3
equiv of DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248
mg), isolation method B: yellow solid (205 mg, 67%). 1H NMR (500
MHz, CDCl3): δ 7.95−8.00 (m, 2H), 7.89−7.93 (m, 2H), 3.36 (s,
3H). 13C{1H} NMR (126 MHz, CDCl3): δ 144.5, 133.5, 129.2, 117.6,
117.3, 42.7. IR (neat): 3090, 2992, 2911, 2231, 1396, 1206, 1178,
1087, 1027, 1006, 964, 845, 833, 785, 748 cm−1. HRMS (ESI-TOF)
m/z: [M + H]+ Calcd for C8H7IN2OS 306.9397; Found 306.9407.
Mp = 100.8−102.4 °C.
N-Iodo-S-pentafluorophenyl-S-phenethyl Sulfoximine (2r). 1r (1
mmol, 304 mg), 2.625 equiv of (NH4)2CO3 (2.625 mmol, 252 mg),
4.025 equiv of DIB (4.025 mmol, 1296 mg), 1.1 equiv of NIS (1.1
mmol, 248 mg), isolation method B: yellow solid (369 mg, 80%). 1H
NMR (500 MHz, CDCl3): δ 7.21−7.28 (m, 2H), 7.11−7.21 (m, 3H),
3.77−4.01 (m, 2H), 3.12−3.34 (m, 2H). 13C{1H} NMR (126 MHz,
CDCl3): δ 143.7−146.3 (m), 143.0−145.6 (m), 136.6−139.1 (m),
136.2, 128.9, 128.6, 127.3, 115.2−116.7 (m), 57.5, 29.6. 19F NMR
(471 MHz, CDCl3): δ −135.8 (d, J = 23.3 Hz, 2F), −143.8 (t, J =
20.8 Hz, 1F), −158.1 (t, J = 20.5 Hz, 2F). IR (neat): 2926, 1639,
1517, 1482, 1230, 1208, 1093, 1026, 980, 743, 691 cm−1. HRMS
(ESI-TOF) m/z: [M + H]+ Calcd for C14H9F5INOS 461.9443;
Found 461.9451. Mp = 103.0−104.1 °C.
N-Iodo-S-phenyl-S-(3-phenylpropyl) Sulfoximine (2s). 1s (1
mmol, 228 mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3
equiv of DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248
mg), isolation method B: light yellow solid (256 mg, 66%). 1H NMR
(500 MHz, CDCl3): δ 7.75−7.80 (m, 2H), 7.64−7.70 (m, 1H),
7.56−7.61 (m, 2H), 7.23−7.27 (m, 2H), 7.16−7.21 (m, 1H), 7.05−
7.09 (m, 2H), 3.44 (ddd, J = 14.0, 11.0, 5.3 Hz, 1H), 3.32 (ddd, J =
14.0, 10.9, 5.1 Hz, 1H), 2.62−2.69 (m, 2H), 2.08−2.19 (m, 1H),
1.92−2.02 (m, 1H). 13C{1H} NMR (126 MHz, CDCl3): δ 139.7,
138.7, 133.7, 129.7, 129.0, 128.7, 128.4, 126.5, 54.3, 34.0, 25.3. IR
(neat): 3052, 2983, 2944, 1605, 1579, 1495, 1445, 1206, 1092, 987,
745, 686 cm−1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for
C15H16INOS 386.0070; Found 386.0087. Mp = 99.3−100.4 °C.
N-Iodo-S,S-diphenyl Sulfoximine (2t). 1t (1 mmol, 186 mg), 1.5
equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3 equiv of DIB (2.3
mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248 mg), isolation
method A: yellow solid (180 mg, 53%). 1H NMR (500 MHz,
CDCl3): δ 7.90−7.98 (m, 4H), 7.54−7.60 (m, 2H), 7.46−7.54 (m,
4H). 13C{1H} NMR (126 MHz, CDCl3): δ 139.4, 133.2, 129.5, 128.4.
IR (neat): 3062, 1445, 1219, 1088, 976, 757, 722, 685 cm−1. HRMS
(ESI-TOF) m/z: [M + H]+ Calcd for C12H10INOS 343.9601; Found
343.9598. Mp = 114.2−114.9 °C.
N-Iodo-S-methyl-S-(4-nitrophenyl) Sulfoximine (2n). 1n (1
mmol, 169 mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3
equiv of DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248
mg), isolation method B: yellow solid (280 mg, 86%). 1H NMR (500
MHz, CDCl3): δ 8.43−8.47 (m, 2H), 8.03−8.10 (m, 2H), 3.38 (s,
3H). 13C{1H} NMR (126 MHz, CDCl3): δ 150.9, 146.1, 129.9, 124.9,
42.9. IR (neat): 3099, 3004, 2918, 1605, 1520, 1343, 1209, 1185,
1088, 1021, 1004, 961, 853, 767, 739, 716, 679 cm−1. HRMS (ESI-
TOF) m/z: [M + H]+ Calcd for C7H7IN2O3S 326.9295; Found
326.9306. Mp = 97.2−100.7 °C.
N-Iodo-S-methyl-S-(2-naphthyl) Sulfoximine (2o). 1o (1 mmol,
174 mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3 equiv of
DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248 mg),
1
isolation method B: pale yellow solid (162 mg, 49%). H NMR (500
MHz, CDCl3): δ 8.47 (d, J = 1.9 Hz, 1H), 8.00−8.06 (m, 2H), 7.93−
7.98 (m, 1H), 7.76 (dd, J = 8.7, 1.9 Hz, 1H), 7.70 (ddd, J = 8.2, 6.9,
1.4 Hz, 1H), 7.65 (ddd, J = 8.0, 6.8, 1.4 Hz, 1H), 3.39 (s, 3H).
13C{1H} NMR (126 MHz, CDCl3): δ 136.8, 135.4, 132.5, 130.6,
130.2, 129.6, 129.5, 128.1, 127.9, 122.8, 42.9. IR (neat): 3003, 2921,
1624, 1590, 1504, 1346, 1267, 1208, 1070, 985, 954, 938, 811, 753,
637 cm−1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C11H10INOS
331.9601; Found 331.9601. Mp = 93.4−94.9 °C.
N-Iodo-dibenzothiophene Sulfoximine (2u). 1u (1 mmol, 184
mg), 1.875 equiv of (NH4)2CO3 (1.875 mmol, 180 mg), 2.875 equiv
of DIB (2.875 mmol, 926 mg), 1.1 equiv of NIS (1.1 mmol, 248 mg),
isolation method A: yellow solid (252 mg, 74%). 1H NMR (500
MHz, CDCl3): δ 7.95−8.00 (m, 2H), 7.79−7.83 (m, 2H), 7.63−7.68
(m, 2H), 7.53−7.59 (m, 2H). 13C{1H} NMR (126 MHz, CDCl3): δ
137.9, 134.0, 132.3, 130.1, 123.2, 121.8. IR (neat): 2987, 1587, 1444,
1195, 1195, 1122, 1066, 978, 948, 753, 709 cm−1. HRMS (ESI-TOF)
m/z: [M + H]+ Calcd for C12H8INOS 341.9444; Found 341.9457.
Mp = 180.0−181.3 °C.
N-Iodo-S-phenethyl-S-phenyl Sulfoximine (2p). 1p (1 mmol, 214
mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3 equiv of DIB
(2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248 mg), isolation
1
method B: orange oil (334 mg, 90%). H NMR (500 MHz, CDCl3):
δ 7.81−7.87 (m, 2H), 7.64−7.70 (m, 1H), 7.56−7.63 (m, 2H), 7.22−
7.27 (m, 2H), 7.17−7.22 (m, 1H), 7.07−7.11 (m, 2H), 3.72 (ddd, J =
14.0, 12.2, 5.0 Hz, 1H), 3.56 (ddd, J = 14.0, 12.0, 4.9 Hz, 1H), 3.13
(ddd, J = 13.9, 12.0, 5.0 Hz, 1H), 2.96 (ddd, J = 13.9, 12.2, 4.9 Hz,
1H). 13C{1H} NMR (126 MHz, CDCl3): δ 138.7, 137.1, 133.8, 129.7,
129.0, 128.9, 128.4, 127.1, 56.3, 29.8. IR (neat): 3059, 3026, 2924,
1602, 1581, 1495, 1445, 1398, 1196, 1088, 1003, 981, 730, 685 cm−1.
HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C14H14INOS 371.9914;
Found 371.9919.
N-Iodo-S-benzyl-S-methyl Sulfoximine (2v). 1v (1 mmol, 138
mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3 equiv of DIB
(2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248 mg), isolation
method B: brown solid (176 mg, 60%). 1H NMR (500 MHz,
CDCl3): δ 7.42 (app. as s, 5H), 4.47−4.56 (m, 2H), 2.89 (s, 3H).
13C{1H} NMR (126 MHz, CDCl3): δ 130.6, 129.4, 129.3, 129.2, 60.9,
38.0. IR (neat): 3001, 2969, 2920, 1493, 1454, 1411, 1210, 1198, 981,
945, 778, 697 cm−1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for
C8H10INOS 295.9601; Found 295.9595. Mp = 81.2−83.8 °C.
N-Iodo-S,S-dimethyl Sulfoximine (2w). DMSO (1 mmol, 78 mg),
1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 1.3 equiv of DIB (1.3
mmol, 419 mg), 1.1 equiv of I2 (1.1 mmol, 279 mg), isolation: orange-
N-Iodo-S-(2-pentafluorophenyethyl)-S-phenyl Sulfoximine (2q).
1q (1 mmol, 304 mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg),
2.3 equiv of DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol,
1
1
248 mg), isolation method B: pale yellow solid (379 mg, 82%). H
brown solid (68 mg, 31%). H NMR (500 MHz, CDCl3): δ 3.21 (s,
6H). 13C{1H} NMR (126 MHz, CDCl3): δ 42.1. IR (neat): 2999,
2918, 1409, 1301, 1167, 1016, 970, 930, 754, 682 cm−1. HRMS (ESI-
TOF) m/z: [M + H]+ Calcd for C2H6INOS 219.9288; Found
219.9286. Mp = 118.4−119.0 °C.
NMR (500 MHz, CDCl3): δ 7.78−7.88 (m, 2H), 7.67−7.74 (m, 1H),
7.56−7.66 (m, 2H), 3.66−3.79 (m, 1H), 3.52−3.64 (m, 1H), 3.14−
3.25 (m, 1H), 3.01−3.14 (m, 1H). 13C{1H} NMR (126 MHz,
1
2
3
CDCl3): δ 145.0 (C-F, JC‑F = 247.3 Hz, JC‑F = 11.9 Hz, JC‑F = 7.9
4
1
2
Hz, JC‑F = 3.8 Hz), 140.4 (C-F, JC‑F = 253.9 Hz, JC‑F = 13.3 Hz,
3JC‑F = 5.3 Hz), 138.0 (s), 136.3−138.7 (m), 134.0 (s), 129.7 (s),
128.8 (s), 110.5 (C-F, 2JC‑F = 18.1 Hz, 3JC‑F = 4.0 Hz), 52.7 (s), 17.3
(s). 19F NMR (471 MHz, CDCl3): δ −143.0 − (−142.9) (m, 2F),
−155.5 (t, J = 20.7 Hz, 1F), −162.2 − (−162.0) (m, 2F). IR (neat):
2987, 1520, 1505, 1208, 1089, 982, 962, 938, 748, 721, 682 cm−1.
HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C14H9F5INOS
461.9443; Found 461.9446. Mp = 115.3−116.4 °C.
N-Iodo-S-(1-dodecyl)-S-methyl Sulfoximine (2x). 1x (1 mmol,
216 mg), 1.5 equiv of (NH4)2CO3 (1.5 mmol, 144 mg), 2.3 equiv of
DIB (2.3 mmol, 741 mg), 1.1 equiv of NIS (1.1 mmol, 248 mg),
1
isolation method B: brown-red solid (156 mg, 42%). H NMR (500
MHz, CDCl3): δ 3.18−3.34 (m, 2H), 3.07 (s, 3H), 1.77−1.86 (m,
2H), 1.40−1.48 (m, 2H), 1.22−1.38 (m, 16H), 0.88 (t, J = 6.8 Hz,
3H). 13C{1H} NMR (126 MHz, CDCl3): δ 54.6, 40.2, 32.0, 29.7,
29.7, 29.6, 29.4, 29.3, 29.1, 28.3, 23.9, 22.8, 14.2. IR (neat): 2916,
5996
J. Org. Chem. 2021, 86, 5991−6000