The Journal of Organic Chemistry
Page 4 of 7
2b (155.8 mg, 90% yield) purified by flash column chromatog-
(d, J = 8.3 Hz, 1H), 8.02 (d, J = 8.6 Hz, 1H), 7.95 (d, J = 8.0 Hz,
2H), 7.60−7.57 (m, 1H), 7.53−7.49 (m, 1H), 6.61 (d, J = 8.0 Hz,
1H), 4.00 (s, 3H). The NMR spectrum was identical to that previ-
ously reported.25
1
2
3
4
5
6
7
8
raphy (Hexane/AcOEt = 3:2) as a white solid; 1H NMR (400MHz,
CDCl3) d = 7.93 (s, 1H), 7.53 (s, 1H), 2.23 (s, 6H), 2.18 (s, 3H).
The NMR spectrum was identical to that previously reported.46
N-(2-iodo-4-methylphenyl)acetamide (2c). According to
the general procedure, 4-methylacetanilide (89.5 mg, 0.6 mmol),
bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH
(171.0 mg, 0.45 mmol) in acetonitrile (2 mL) for 13 h to afford 2c
(150.4 mg, 91% yield) purified by flash column chromatography
1-iodo-2-methoxynaphthalene (2j). According to the gen-
eral procedure, 2-methoxynaphthalene (94.9 mg, 0.6 mmol), bis(4-
methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH (171.0 mg,
0.45 mmol) in acetonitrile (2 mL) for 30 min to afford 2j (146.0
mg, 82% yield) purified by flash column chromatography (Hex-
ane/AcOEt = 9:1) as a white solid; 1H NMR (500MHz, CDCl3) d =
8.14 (d, J = 8.5 Hz, 1H), 7.84 (d, J = 8.9 Hz, 1H), 7.75 (d, J = 8.3
Hz, 2H), 7.56-7.53 (m, 1H), 7.40-7.37 (m, 1H), 7.22 (d, J = 8.9 Hz,
1H), 4.03 (s, 3H). The NMR spectrum was identical to that previ-
ously reported.25
1-iodo-2,4,6-trimethoxybenzene (2k). According to the
general procedure, 1,3,5-trimethoxybenzene (100.9 mg, 0.6 mmol),
bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH
(125.4 mg, 0.33 mmol) in acetonitrile (2 mL) for 15 min to afford
2l (167.6 mg, 95% yield) purified by flash column chromatography
(Hexane/AcOEt = 9:1) as a white solid; 1H NMR (500MHz,
CDCl3) d = 6.15 (s, 2H), 3.87 (s, 6H), 3.83 (s, 3H). The NMR spec-
trum was identical to that previously reported.25
1-iodo-2,4,6-trimethylbenzene (2l). According to the gen-
eral procedure, 1,3,5-trimethylbenzene (82.9 µL, 0.6 mmol), bis(4-
methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH (125.4 mg,
0.33 mmol) in acetonitrile (2 mL) for 1.5 h to afford 2k (110.0 mg,
74% yield) purified by flash column chromatography (Hexane/Ac-
OEt = 9:1) as a white solid; 1H NMR (500MHz, CDCl3) d = 6.89
(s, 2H), 2.43 (s, 6H), 2.24 (s, 3H). The NMR spectrum was identical
to that previously reported.25
4-iodo-1,2-dimethylbenzene/1-iodo-2,3-dimethylben-
zene (2m/2m’; 5/1). According to the general procedure, o-xy-
lene (72.4 µL, 0.6 mmol), bis(4-methoxyphenyl) disulfide 3c (1.7
mg, 6 µmol) and DIH (171.0 mg, 0.45 mmol) in acetonitrile (2 mL)
for 24 h to afford 2m/2m’ as inseparable mixture (110.1 mg, 79%
yield) purified by flash column chromatography (Hexane/AcOEt =
95:5) as a colorless oil; 1H NMR (400MHz, CDCl3) d = 7.67 (d, J
= 7.9 Hz, 0.2 × 1H), 7.46 (s, 1.0 × 1H), 7.40 (d, J = 7.9 Hz, 1.0 ×
1H), 7.09 (d, J = 7.5 Hz, 0.2 × 1H), 6.85 (d, J = 7.9 Hz, 1.0 × 1H),
6.76 (dd, J = 7.9 7.5 Hz, 0.2 × 1H), 2.40 (s, 0.2 × 3H), 2.33 (s, 0.2
× 3H), 2.19 (s, 1.0 × 6H). The NMR spectra were identical to those
previously reported.25
1
(Hexane/AcOEt = 3:2) as a pale pink solid; H NMR (400MHz,
CDCl3) d = 8.03 (d, J = 8.3 Hz, 1H), 7.61 (s, 1H), 7.32 (br, 1H),
7.15 (d, J = 8.3 Hz, 1H), 2.28 (s, 3H), 2.23 (s, 3H). The NMR spec-
trum was identical to that previously reported.47
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
N-(3-fluoro-4-iodophenyl)acetamide (2d). According to
the general procedure, 3-fluoroacetanilide (91.9 mg, 0.6 mmol),
bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH
(171.0 mg, 0.45 mmol) in acetonitrile (2 mL) for 1.5 h to afford 2d
(162.9 mg, 97% yield) purified by flash column chromatography
(Hexane/AcOEt = 3:2) as a white solid; 1H NMR (500MHz,
DMSO-d6) d = 10.23 (s, 1H), 7.71 (dd, J = 8.6, 7.5 Hz, 1H), 7.65
(dd, J = 10.9, 2.3 Hz, 1H), 7.11 (dd, J = 8.6, 2.3 Hz, 1H), 2.04 (s,
3H);13C{1H } NMR (100MHz, DMSO-d6) d = 168.8, 162.2, 159.8,
141.3, 141.2, 138.9, 138.8, 116.7, 106.2, 105.9, 73.2, 73.0, 24.1;
HRMS (ESI) m/z: [M − H]− Calcd for C8H6NOFI 277.9484; Found:
277.9492.
N-(2-chloro-4-iodophenyl)acetamide (2e). According to
the general procedure, 2-chloroacetanilide (101.8 mg, 0.6 mmol),
bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH
(171.0 mg, 0.45 mmol) in acetonitrile (2 mL) for 13 h to afford 2e
(172.8 mg, 97% yield) purified by flash column chromatography
(Hexane/AcOEt = 3:2) as a white solid; 1H NMR (400MHz,
CDCl3) d = 8.17 (d, J = 8.8 Hz, 1H), 7.70 (d, J = 2.0 Hz, 1H),
7.58−7.55 (m, 2H), 2.24 (s, 3H). The NMR spectrum was identical
to that previously reported.17
N-(4-iodophenyl)-4-methylbenzenesulfonamide
(2f).
According to the general procedure, 4-methyl-N-phenylbenzene-
sulfonamide (148.4 mg, 0.6 mmol), bis(4-methoxyphenyl) disul-
fide 3c (1.7 mg, 6 µmol) and DIH (171.0 mg, 0.45 mmol) in ace-
tonitrile (2 mL) for 2.5 h to afford 2f (217.1 mg, 97% yield) purified
by flash column chromatography (Hexane/AcOEt = 3:2) as a white
solid; 1H NMR (400MHz, CDCl3) d = 7.65 (d, J = 8.3 Hz, 2H), 7.54
(d, J = 8.5 Hz, 2H), 7.25 (d, J = 8.2 Hz, 2H), 6.83 (d, J = 8.5 Hz,
2H), 6.64 (s, 1H), 2.39 (s, 3H). The NMR spectrum was identical
to that previously reported.48
1-(tert-butyl)-4-iodobenzene (2n). According to the general
procedure, tert-butylbenzene (92.6 µL, 0.6 mmol), bis(4-methoxy-
phenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH (125.4 mg, 0.33
mmol) in acetonitrile (2 mL) for 24 h to afford 2n (60.8 mg, 39%
yield) purified by flash column chromatography (Hexane/AcOEt =
95:5) as a colorless oil; 1H NMR (400MHz, CDCl3) d = 7.60 (d, J
= 8.1 Hz, 1H), 7.13 (d, J = 8.1 Hz, 1H), 1.29 (s, 9H). The NMR
spectrum was identical to that previously reported.49
1-iodo-4-methoxybenzene (2g). According to the general
procedure, anisole (65.2 µL, 0.6 mmol), bis(4-methoxyphenyl) di-
sulfide 3c (1.7 mg, 6 µmol) and DIH (171.0 mg, 0.45 mmol) in
acetonitrile (2 mL) for 30 min to afford 2g (133.5 mg, 95% yield)
purified by flash column chromatography (Hexane/AcOEt = 9:1)
1
as a white solid; H NMR (500MHz, CDCl3) d = 7.56 (d, J = 9.2
1-(3-iodo-1H-indol-1-yl)ethan-1-one (2o). According to the
general procedure, 1-acetylindole (68.9 µL, 0.6 mmol), bis(4-meth-
oxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH (171.0 mg, 0.45
mmol) in acetonitrile (2 mL) for 13 h to afford 2o (116.7 mg, 68%
yield) purified by flash column chromatography (Hexane/AcOEt =
3:1) as a brown solid; 1H NMR (500MHz, CDCl3) d = 8.41 (d, J =
8.0 Hz, 1H), 7.59 (s, 1H), 7.44−7.36 (m, 3H), 2.65 (s, 3H). The
NMR spectrum was identical to that previously reported.50
3-iodo-1-[(4-methylphenyl)sulfonyl]-1H-indole (2p). Ac-
cording to the general procedure, 1-tosylindole (162.8 mg, 0.6
mmol), bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and
DIH (171.0 mg, 0.45 mmol) in acetonitrile (2 mL) for 30 min to
afford 2p (170.2 mg, 71% yield) purified by flash column chroma-
Hz, 2H), 6.68 (d, J = 9.2 Hz, 2H), 3.78 (s, 3H). The NMR spectrum
was identical to that previously reported.25
2-iodo-5-methoxybenzaldehyde (2h). According to the
general procedure, 3-methoxybenzaldehyde (72.9 µL, 0.6 mmol),
bis(4-methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH
(171.0 mg, 0.45 mmol) in acetonitrile (2 mL) for 19 h to afford 2h
(129.0 mg, 82% yield) purified by flash column chromatography
(Hexane/AcOEt = 9:1) as a white solid; 1H NMR (500MHz,
CDCl3) d = 10.02 (s, 1H), 7.81 (d, J = 8.6 Hz, 1H), 7.43 (d, J = 3.2
Hz, 1H), 6.92 (dd, J = 8.6, 3.2 Hz, 1H), 3.85 (s, 3H). The NMR
spectrum was identical to that previously reported.25
1-iodo-4-methoxynaphthalene (2i). According to the gen-
eral procedure, 1-methoxynaphthalene (86.3 µL, 0.6 mmol), bis(4-
methoxyphenyl) disulfide 3c (1.7 mg, 6 µmol) and DIH (171.0 mg,
0.45 mmol) in acetonitrile (2 mL) for 30 min to afford 2i (146.5 mg,
82% yield) purified by flash column chromatography (Hexane/Ac-
OEt = 9:1) as a brown solid; 1H NMR (500MHz, CDCl3) d = 8.23
1
tography (Hexane/AcOEt = 3:1) as a pale yellow solid; H NMR
(500MHz, CDCl3) d = 7.96 (d, J = 8.9 Hz, 1H), 7.78 (d, J = 8.3 Hz,
2H), 7.70 (s, 1H), 7.39−7.29 (m, 3H), 7.24 (d, J = 8.0 Hz, 2H), 2.36
ACS Paragon Plus Environment