An improved protocol for regioselective ring-opening of sulfonyl aziridines with iodine promoted by PPh3

Article abstract of DOI:10.1002/cjoc.201300625

A new route to synthesize β-iodo amines from sulfonyl aziridines and iodine was developed in the presence of PPh₃. This ring-opening reaction was an efficient and simple process to give β-iodo amines in excellent yields with high chemoselectivi

Full text of DOI:10.1002/cjoc.201300625

FULL PAPER
DOI: 10.1002/cjoc.201300625
An Improved Protocol for Regioselective Ring-Opening of
Sulfonyl Aziridines with Iodine Promoted by PPh3
Jinfeng Zhang, Lingguo Meng,* Chuntao Li, and Guoyuan Xiao
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
A new route to synthesize β-iodo amines from sulfonyl aziridines and iodine was developed in the presence of
PPh3. This ring-opening reaction was an efficient and simple process to give β-iodo amines in excellent yields with
high chemoselectivity.
Keywords sulfonyl aziridines, iodine, ring-opening, β-iodo amines, PPh3
Introduction
a solution of 2-phenyl-1-tosylaziridine (1a) and iodine
under various reaction conditions, and the results are
shown in Table 1. Treatment of 1a with 0.5 equiv. of
iodine and 0.5 equiv. of PPh3 in CH2Cl2 at room tem-
perature in 1 min afforded N-(2-iodo-2-phenylethyl)-4-
methylbenzenesulfonamide (2a) in 96% yield (Table 1,
Entry 1). The yield of 2a could not be further improved
by increasing the amount of PPh3, but decreased sharply
when 0.2 equiv. of PPh3 was added in the reaction (Ta-
ble 1, Entries 2 and 3). 35% yield of 2a was obtained
when 0.2 equiv. of iodine was used and the yield was
failure to further increase when 1.0 equiv. of iodine was
used. Solvent screening revealed a significant solvent
effect. When shifting the solvent to CHCl3, toluene,
dioxane, or THF, the desired product 2a was obtained in
85%, 81%, 75% or 70% yield, respectively (Table 1,
Entries 6－9). With use of CCl4, CH3CN or DMF as a
solvent, product 2a was isolated in low yields (Table 1,
Entries 10－12). Only a trace amount of the 2a was de-
tected by TLC when DMSO was used as solvent (Table
1, Entry 13).
Aziridines are one kind of the most important inter-
mediates in organic synthesis and have served as key
building blocks in the preparation of various nitrogen-
containing molecules.[1] On the other hand, aziridines
have covered many interesting reactions, such as ring
expansion,[2] cyclization,[3] isomerization,[4] N-aryla-
tion,[5] etc. Apart from above reactions, the ring-opening
of aziridines has been also studied intensively and nu-
merous synthetic methods have been developed to real-
ize the opening of aziridine rings.[6] Here, we focused
on the preparation of β-iodo amines[7] by using sulfonyl
aziridines as starting materials in the presence of PPh3
and iodine.
To our best knowledge, the usual preparative meth-
ods are regioselective ring-opening of aziridines with
tetraalkylammonium halides by using the following re-
agents, such as β-cyclodextrin,[8a] ammonium-12-
molybdophosphate[8b] and BF3•OEt2,[8c] as catalyst or
promoter. On the other hand, the β-iodo amines also
With the optimized reaction conditions in hand, a
variety of substituted aziridines reacted with iodine
smoothly to generate the corresponding ring-opening
products in excellent yields with high chemoselectivity
and the results were summarized in Table 2. Clearly,
aziridines bearing the substitutes on the para-positions
of benzene rings have no obvious effect on the yields of
the reactions. Aziridines with electron-withdrawing
groups, such as F, Cl, and Br on the para-positions of
benzene rings reacted with iodine to give the corre-
sponding products 2b－2d in 95%－97% yields (Table
2, Entries 2－4). However, the reaction became com-
plicated and no desired product was isolated when
2-(4-methoxyphenyl)-1-tosylaziridine was used as sub-
strate, which might be ascribed to the unstable chemical
could be obtained through ring-opening of aziridines in
[9b]
the presence of CeCl3,[9a] ZnI2
and ionic liquid.[9c]
Except above synthetic methods, Wu also reported
thiophenol promoted efficient ring-opening of aziridines
with iodine to synthesize β-iodo amines, but thiphenol is
one of disagreeable, sick and harmful materials.[10]
Herein, we describe an alternative methodology to syn-
thesize β-iodo amines by iodination of aziridines using
molecular iodine and PPh3. It should be noted that better
regioselectivity was observed than Wu’s methods in
some extent.
Results and Discussion
Our studies were initiated by the addition of PPh3 to
*
E-mail: milig@126.com; Tel.: 0086-0561-3802047
Received August 18, 2013; accepted October 24, 2013; published online November 14, 2013.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201300625 or from the author.
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Chin. J. Chem. 2013, 31, 1508—1512

An Improved Protocol for Regioselective Ring-Opening of Sulfonyl Aziridines with Iodine
Table 1 Ring-opening of aziridine 1a with iodine in the pres-
ence of PPh3
property of the desired product. The ortho-position ef-
fect of aziridine was not observed in the reaction of
2-(2-chlorophenyl)-1-tosylaziridine with iodine, which
generated the product 2f in 90% yield. 97% and 94%
yields were obtained when 3-chlorophenyl- and
3-bromophenyl-1-tosylaziridine were proceeded in the
reaction, respectively. Furthermore, 2-(naphthalen-2-
yl)-1-tosylaziridine could be converted to desired prod-
ucts in 96% yield. Aliphatic aziridines, such as 2-hex-
yl-1-tosylaziridine and 7-tosyl-7-azabicyclo[4.1.0]hep-
tane, also afforded corresponding ring-opening products
in excellent yields, and it is important to note that only
single ring-opening product was found and better
chemoselectivity was observed compared to previous
synthetic methods (Table 2, Entry 10).[10] On the other
hand, the reactions of 4-bromophenylsulfonyl- and
4-chlorophenylsulfonyl-2-phenylaziridine with iodine
also gave corresponding products in 95% and 93%
yields, respectively.
a
I
I2 (0.5 equiv.)
Ts
NHTs
PPh3 (0.5 equiv.)
N
Solvent, r.t., < 1 min
1a
2a
Entry I2 (equiv.)
PPh3 (equiv.)
Solvent
Yieldb/%
96
1
2
1/2
1/2
1/2
1/5
1.0
1/2
1/2
1/2
1/2
1/2
1/2
1/2
1/2
1/2
1/5
1.0
1/2
1/2
1/2
1/2
1/2
1/2
1/2
1/2
1/2
1/2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CHCl3
Toluene
Dioxane
THF
48
3
96
4
35
5
93
6
85
7
81
8
75
9
70
10
11
12
13
CCl4
35
CH3CN
DMF
30
To further evaluate the scope of the ring-opening
reaction, epoxides were examined under the above op-
timized reaction conditions. It would be seen from
Scheme 1, 7-oxabicyclo[4.1.0]heptane and 2-phenyl-
oxirane reacted with iodine smoothly to generate iodo-
hydrins products in 85% and 95% yields, respectively.
20
DMSO
trace
a
Reaction conditions: 1a (0.2 mmol), I2 (amount indicated in
Table 1), PPh3 (amount indicated in Table 1), solvent (2.0 mL),
r.t., in air, ＜1 min. b Isolated yields.
Table 2 PPh3-mediated ring-opening reaction of aziridinesa
R1
R2
I2 (0.5 equiv.)
PPh3 (0.5 equiv.)
O
O
O
O
I
H
R3
R3
N S
N S
R1
<1 min
CH2Cl2, r.t.
R2
1
2
Entry
1
Aziridine, 1
Product, 2
Yieldb/%
96
Ts
I
H
N
N
Ts
2a
1a
I
Ts
H
N
N
F
Cl
Br
2
3
4
5
Ts
Ts
Ts
97
1b
2b
F
Ts
Ts
I
H
N
N
96
95
2c
Cl
Br
1c
I
H
N
N
2d
1d
Ts
N
H3CO
2e was not detected
complicated
1e
Chin. J. Chem. 2013, 31, 1508—1512
© 2013 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
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Zhang et al.
FULL PAPER
Continued
Entry
6
Aziridine, 1
Product, 2
Yieldb/%
Cl
Cl
I
Ts
H
N
N
90
97
94
Ts
2f
1f
Cl
Br
I
Ts
H
N
Cl
Br
N
7
8
Ts
2g
1g
I
Ts
H
N
N
Ts
Ts
2h
1h
Ts
I
N
H
N
9
96
2i
1i
1j
Ts
N
I
NHTs
10
11
93
91
C6H13
C6H13
2j
NHTs
I
NTs
1k
2k
Cl
Br
O
O
I
O
H
N S
Cl
Br
S
12
95
93
N
N
O
2l
1l
O
S
O
I
H
N S
13
O
O
2m
1m
a 1a (0.2 mmol), I2 (0.1 mmol), PPh3 (0.1 mmol), CH2Cl2 (2.0 mL), r.t., in air, ＜1 min. b Isolated yield.
Scheme 1 PPh3-mediated ring-opening reaction of epoxides
pared with previous reports, the synthetic method has
some merits: (1) easier to manipulate; (2) without any
metals; (3) better regioselectivity in some extent than
Wu’s methods.
OH
O
3a
I2 (0.5 equiv.)
PPh3 (0.5 equiv.)
I
4a 85%
Experimental
CH2Cl2, r.t., <1 min
O
I
All reactions were conducted in oven-dried glass-
ware with magnetic stirring. Chromatographic purifica-
tion was performed on silica gel (100－200 mesh) and
analytical thin layer chromatography (TLC) on silica gel
60-F254 (Qindao), which was detected by fluorescence.
1H NMR (400 MHz) and 13C NMR (100 MHz) spectra
were measured with a Bruker AC 400 spectrometer with
CDCl3 or d6-DMSO as solvent and recorded relative to
internal tetramethylsilane standard. High resolution
mass spectra were obtained with a Micromass GCT-
OH
3b
4b 95%
Conclusions
In conclusion, we have described a new route to
synthesize β-iodo amines from sulfonyl aziridines and
iodine in the presence of PPh3 and these methods are
also suitable for the ring-opening of epoxides. Com-
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Chin. J. Chem. 2013, 31, 1508—1512

An Improved Protocol for Regioselective Ring-Opening of Sulfonyl Aziridines with Iodine
TOF mass spectrometer. IR spectra were recorded as
thin films or as solids in KBr pellets on a Perkin-Elmer
FT210 spectrophotometer. Melting points were deter-
mined on a digital melting point apparatus and tem-
peratures were uncorrected.
NMR (400 MHz, d6-DMSO) δ: 8.09 (t, J＝6.0 Hz, 1H),
7.65 (d, J＝8.0 Hz, 2H), 7.43 (s, 1H), 7.36－7.16 (m,
5H), 5.16－5.13 (m, 1H), 3.49－3.45 (m, 2H), 2.36 (s,
3H); 13C NMR (100 MHz, CDCl3) δ: 143.8, 143.2,
138.0, 133.5, 130.8, 130.1, 128.4, 128.0, 127.0, 126.8,
50.6, 29.4, 21.4; IR (KBr) v: 3287, 2925 cm−1; HRMS
(ESI) calcd for C15H1635ClINO2S (M＋H)＋ 435.9635;
found 435.9631.
General procedure for the preparation of β-iodo-
amines or iodohydrins
To a solution of aziridines 1 or epoxide 3 (0.20
mmol) and iodine (0.10 mmol) in CH2Cl2 (2.0 mL) was
added PPh3 (0.10 mmol), and the reaction mixture was
stirred at room temperature in 1 min. Then the mixture
was purified directly by flash column chromatography
on silica gel to afford the corresponding product.
N-(2-Iodo-2-phenylethyl)-4-methylbenzenesulfon-
amide (2a)[9a] 1H NMR (400 MHz, CDCl3) δ: 7.72 (d,
J＝8.0 Hz, 2H), 7.33 (d, J＝8.0 Hz, 2H), 7.26 (s, 5H),
5.04 (t, J＝7.6 Hz, 1H), 4.97 (t, J＝6.4 Hz, 1H), 3.73－
3.66 (m, 1H), 3.55－3.48 (m, 1H), 2.45 (s, 3H); 13C
NMR (75 MHz, CDCl3) δ: 143.8, 139.9, 137.0, 129.9,
129.0, 128.7, 127.5, 127.0, 51.2, 29.9, 21.6.
N-(2-(3-Bromophenyl)-2-iodoethyl)-4-methylben-
zenesulfonamide (2h) White solid 122－125 ℃; 1H
NMR (400 MHz, d6-DMSO) δ: 8.09 (t, J＝6.0 Hz, 1H),
7.65 (d, J＝8.0 Hz, 2H), 7.55 (s, 1H), 7.43－7.34 (m,
4H), 7.24 (d, J＝8.0 Hz, 1H), 5.15－5.11 (m, 1H),
3.48－3.45 (m, 2H), 2.36 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 144.1, 143.2, 138.0, 131.3, 131.1, 130.8,
130.1, 127.4, 126.8, 122.0, 50.7, 29.4, 21.4; IR (KBr) v:
3287, 2925 cm−1; HRMS (ESI) calcd for C15H1679Br-
INO2S (M＋H)＋ 479.9130; found 479.9126.
N-(2-Iodo-2-(naphthalen-2-yl)ethyl)-4-methylben-
1
zenesulfonamide (2i) White solid 141－142 ℃; H
NMR (400 MHz, d6-DMSO) δ: 8.12 (t, J＝6.0 Hz, 1H),
7.86－7.84 (m, 4H), 7.66 (d, J＝8.0 Hz, 2H), 7.51－
7.49 (m, 3H), 7.32 (d, J＝8.0 Hz, 2H), 5.38－5.34 (m,
1H), 3.62－3.55 (m, 2H), 2.33 (s, 3H); 13C NMR (100
MHz, CDCl3) δ: 143.2, 138.7, 138.1, 133.0, 130.0,
128.8, 128.3, 127.9, 126.9, 126.9, 126.8, 126.5, 126.3,
50.9, 32.3, 21.4; IR (KBr) v: 3278, 2930 cm−1; HRMS
(EI) calcd for C19H18NO2S (M＋−I) 324.1058; found
324.1054.
N-(2-Iodooctyl)-4-methylbenzenesulfonamide
(2j)[11] 1H NMR (400 MHz, CDCl3) δ: 7.79 (d, J＝8.0
Hz, 2H), 7.31 (d, J＝8.0 Hz, 2H), 5.00 (d, J＝8.0 Hz,
1H), 3.26－3.15 (m, 2H), 2.98－2.94 (m, 2H), 2.42 (s,
3H), 1.49－1.34 (m, 2H), 1.25－1.05 (m, 8H), 0.85 (t,
J＝7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ: 143.5,
137.8, 129.7, 127.0, 52.7, 35.3, 31.5, 28.6, 25.1, 22.4,
21.5, 14.4, 14.0.
N-(2-Iodocyclohexyl)-4-methylbenzenesulfonamide
(2k)[9a] 1H NMR (400 MHz, CDCl3) δ: 7.81 (d, J＝8.0
Hz, 2H), 7.32 (d, J＝8.0 Hz, 2H), 5.26 (d, J＝6.4 Hz,
1H), 4.02－3.97 (m, 1H), 3.31－3.27 (m, 1H), 2.42 (s,
3H), 2.35－2.33 (m, 1H), 2.19－2.16 (m, 1H), 1.99－
1.89 (m, 1H), 1.68－1.66 (m, 1H), 1.53－1.50 (m, 1H),
1.41－1.22 (m, 3H); 13C NMR (100 MHz, CDCl3) δ:
143.5, 137.4, 129.6, 127.3, 59.1, 34.9, 32.9, 29.6, 26.5,
26.5, 21.5.
4-Chloro-N-(2-iodo-2-phenylethyl)benzenesulfon-
amide (2l) White solid 151－153 ℃; 1H NMR (400
MHz, d6-DMSO) δ: 8.26 (t, J＝6.0 Hz, 1H), 7.78 (d,
J＝8.8 Hz, 2H), 7.62 (d, J＝8.8 Hz, 2H), 7.38 (d, J＝
7.2 Hz, 2H), 7.30－7.21 (m, 3H), 5.19－5.15 (m, 1H),
3.55－3.40 (m, 2H); 13C NMR (100 MHz, CDCl3) δ:
141.3, 139.8, 137.8, 129.8, 129.0. 128.8, 128.6, 128.1,
50.9, 31.7; IR (KBr) v: 3291, 2923 cm−1; HRMS (EI)
calcd for C14H1335ClNO2S (M＋ −I) 294.0356; found
294.0354.
N-(2-(4-Fluorophenyl)-2-iodoethyl)-4-methylben-
1
zenesulfonamide (2b) White solid 141－143 ℃; H
NMR (400 MHz, d6-DMSO) δ: 8.05 (t, J＝5.6 Hz, 1H),
7.65 (d, J＝8.4 Hz, 2H), 7.44－7.40 (m, 2H), 7.36 (d,
J＝8.4 Hz, 2H), 7.13－7.08 (m, 2H), 5.20－5.16 (m,
1H), 3.49－3.36 (m, 2H), 2.36 (s, 3H); 13C NMR (100
MHz, CDCl3) δ: 163.1 (d, J＝243.8 Hz), 143.2, 138.0,
137.8 (d, J＝3.2 Hz), 130.3 (d, J＝8.4 Hz), 130.1, 126.8,
115.9 (d, J＝21.4 Hz), 51.1, 30.5, 21.4; IR (KBr) v:
3280, 2925 cm−1; HRMS (EI) calcd for C15H15FNO2S
(M＋−I): 292.0808; found 292.0803.
N-(2-(4-Chlorophenyl)-2-iodoethyl)-4-methylben-
zenesulfonamide (2c)[9a]
1H NMR (400 MHz,
d6-DMSO) δ: 8.05 (t, J＝5.6 Hz, 1H), 7.64 (d, J＝8.4
Hz, 2H), 7.40 (d, J＝8.4 Hz, 2H), 7.35－7.31 (m, 4H),
5.17－5.13 (m, 1H), 3.47－3.39 (m, 2H), 2.36 (s, 3H);
13C NMR (100 MHz, CDCl3) δ: 143.2, 140.5, 138.0,
132.9, 130.1, 129.0, 126.8, 50.9, 29.9, 21.4.
N-(2-(4-Bromophenyl)-2-iodoethyl)-4-methylben-
zenesulfonamide (2d)[8a]
1H NMR (400 MHz,
d6-DMSO) δ: 8.05 (t, J＝6.0 Hz, 1H), 7.64 (d, J＝8.4
Hz, 2H), 7.47 (d, J＝8.4 Hz, 2H), 7.39－7.31 (m, 4H),
5.17－5.13 (m, 1H), 3.50－3.38 (m, 2H), 2.36 (s, 3H);
13C NMR (100 MHz, CDCl3) δ: 143.2, 140.9, 138.0,
131.9, 130.3, 130.1, 126.8, 121.5, 50.8, 29.9, 21.4.
N-(2-(2-Chlorophenyl)-2-iodoethyl)-4-methylben-
1
zenesulfonamide (2f) Colorless oil. H NMR (400
MHz, d6-DMSO) δ: 8.14 (t, J＝6.0 Hz, 1H), 7.67 (d,
J＝8.0 Hz, 2H), 7.60 (dd, J＝8.4, 1.2 Hz, 1H), 7.41－
7.28 (m, 5H), 5.42－5.38 (m, 1H), 3.55－3.51 (m, 2H),
2.36 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 143.3,
138.4, 137.9, 132.6, 130.2, 130.1, 129.1, 128.3, 126.8,
49.6, 26.0, 21.4; IR (neat) v: 3285, 2920 cm−1; HRMS
(EI) calcd for C15H1535ClNO2S (M−I)＋ 308.0512; found
308.0525.
4-Bromo-N-(2-iodo-2-phenylethyl)benzenesulfon-
N-(2-(3-Chlorophenyl)-2-iodoethyl)-4-methylben-
zenesulfonamide (2g) White solid 124－126 ℃; H
amide (2m) White solid 150－152 ℃; 1H NMR (400
1
Chin. J. Chem. 2013, 31, 1508—1512
© 2013 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1511

Zhang et al.
FULL PAPER
T. Org. Lett. 2011, 13, 1110.
MHz, d6-DMSO) δ: 8.26 (t, J＝6.0 Hz, 1H), 7.77 (d,
J＝8.8 Hz, 2H), 7.70 (d, J＝8.8 Hz, 2H), 7.38 (d, J＝
7.2 Hz, 2H), 7.30－7.23 (m, 3H), 5.18－5.14 (m, 1H),
3.55－3.39 (m, 2H); 13C NMR (100 MHz, CDCl3) δ:
141.3, 140.2, 132.7, 129.0, 128.9, 128.6, 128.1, 126.7,
50.9, 31.7; IR (KBr) v: 3290, 2920 cm−1; HRMS (EI)
calcd for C14H1379BrNO2S (M＋ −I) 337.9850; found
337.9844.
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2-Iodocyclohexanol (4a)[10] 1H NMR (400 MHz,
CDCl3) δ: 4.06－4.00 (m, 1H), 3.68－3.62 (m, 1H),
2.48－2.42 (m, 2H), 2.12－1.98 (m, 2H), 1.85－1.82
(m, 1H), 1.44－1.20 (m, 3H); 13C NMR (100 MHz,
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Chem. 2004, 69, 689.
2-Iodo-2-phenylethanol (4b)[10] 1H NMR (400
MHz, CDCl3) δ: 7.44 (d, J＝7.2 Hz, 2H), 7.32－7.27 (m,
3H), 5.21－5.18 (m, 1H), 4.11－4.06 (m, 1H), 2.21 (s,
1H); 13C NMR (100 MHz, CDCl3) δ: 140.0, 128.9,
128.5, 127.9, 68.6, 35.6.
Acknowledgement
We express our appreciation to the Anhui Provincial
Natural Science Foundation (No. 1208085QB40).
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