Nitrite ionic liquid as a new reagent for in situ synthesis of aryl iodides and azides

Article abstract of DOI:10.1007/s11164-013-1505-5

A new ionic liquid, 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy] ethyl)-1H-imidazol-3-ium dinitrite, was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of aryl amines into their corresponding diazonium salts, which were converted into aryl iodides and aryl azides using potassium iodide or sodium azide, respectively. Various aryl amines possessing electron-withdrawing groups or electron-donating groups were converted into the corresponding aryl iodides and aryl azides in excellent yields. Advantages of this methodology are the use of mild reaction conditions, short reaction times, and avoiding the use of toxic solvents.

Full text of DOI:10.1007/s11164-013-1505-5

Res Chem Intermed
DOI 10.1007/s11164-013-1505-5
Nitrite ionic liquid as a new reagent for in situ synthesis
of aryl iodides and azides
Hossein Eshghi
Marjan Ghasemzadeh
•
Mehdi Bakavoli
•
Received: 22 August 2013 / Accepted: 2 December 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract A new ionic liquid, 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-
yl)ethyloxy] ethyl)-1H-imidazol-3-ium dinitrite, was synthesized. This ionic liquid
was used as a convenient nitrosonium source in diazotization of aryl amines into
their corresponding diazonium salts, which were converted into aryl iodides and aryl
azides using potassium iodide or sodium azide, respectively. Various aryl amines
possessing electron-withdrawing groups or electron-donating groups were con-
verted into the corresponding aryl iodides and aryl azides in excellent yields.
Advantages of this methodology are the use of mild reaction conditions, short
reaction times, and avoiding the use of toxic solvents.
Keywords Ionic liquid Á Aromatic amines Á Iodination Á Azidation Á
Potassium iodide Á Sodium azide
Introduction
Arenediazonium salts have gained attention in synthetic chemistry due to their
powerful synthetic as well as industrial importance [1–3]. It is well documented that
arenediazonium salts [4, 5] are very reactive intermediates for various organic
conversions. They electrochemically reduce into radicals or cations that immedi-
ately attach covalently to appropriate reactive species like radicals or anions.
It is well known that aromatic halides are important building blocks in organic
transformations, such as the Suzuki cross-coupling and Heck-type reactions [6–12],
and one of the most renowned methods for the synthesis of aryl halides from aryl
amines is the traditional Sandmeyer reaction [13–16]. Recently, some new versions
H. Eshghi (&) Á M. Bakavoli Á M. Ghasemzadeh
Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad,
P.O. Box 91775-1436, Mashhad, Iran
e-mail: heshghi@um.ac.ir
123

H. Eshghi et al.
have been reported for introducing iodine into an aromatic substrate by a sequence
involving diazotization–iodination of corresponding amines, such as HI/KNO in
2
DMSO [17], KI/NaNO /PTSA in MeCN [18], NaNO /sulfonated-resin/KI in H O
2
2
2
-
[19], PTSA/NaNO /KI in water-paste form [20], resin NO2 , p-TsOH, H O [21],
2 2
wet SSA/NaNO /KI [22], and wet CSA/NaNO /KI [23].
2
2
At the same time, aryl azides are useful intermediates in the synthesis of various
heterocyclic compounds and transition metal complexes [24–26]. More recently,
they have also been utilized to constitute important components in many functional
materials such as photoaffinity-labeling probes for proteins [27–30]. Despite these
interesting applications, very few synthetic methods have been developed to
synthesize aryl azides from readily available starting materials [31]. A number of
methods have been developed to synthesize aryl azides, for example: reaction of
aryl amine with TfN , CuSO and triethylamine [32], direct coupling of arylhalides
3
4
[
33], or arylboronicacids [34], with NaN3 catalyzed by copper salts, and
combination of aryl amines with t-BuONO followed by addition of NaN3 or
TMSN3 [34]. Hence, there is still considerable interest in developing simple
methods for synthesis of aryl iodides and aryl azides that preferably have a low
manufacturing cost while minimizing environmental pollution.
We would like to present the direct convenient one-pot synthesis of aryl iodides
and aryl azides from aryl amines using 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-
ium-3-yl)ethyloxy] ethyl)-1H-imidazol-3-ium dinitrite (1b) as a new ionic liquid
that can act as nitrosonium ion for the efficient conversion of aryl amines to their
corresponding diazonium salts under mild reaction conditions (Scheme 1).
Experimental
All the aniline derivatives were purchased from Fluka and Merck. The reaction was
monitored by TLC using silica gel plates and the products were identified by
comparison of their spectra and physical data with those of the authentic samples.
1
13
H and C NMR spectra were measured at 400 MHz on a Bruker spectrometer with
tetramethylsilane (Me Si) as an internal reference and CDCl as the solvent for aryl
4
3
iodides and aryl azides. Melting points were determined in open capillary tubes in
an Electrothermal IA 9000 melting point apparatus. IR spectra were recorded on an
Avatar 370 FT-IR Thermo Nicolet Infrared spectrophotometer.
Preparation of 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]
ethyl)-1H-imidazol-3-ium dichloride (1a)
A mixture of 1-methylimidazole (4.85 g, 58.5 mmol) and 1-chloro-2-(2-chloroeth-
oxy)ethane (2.3 ml, 26.6 mmol) was stirred in DMF (40 ml) at 120 °C for 2 h.
After cooling the mixture, we extracted the residue oil, and then the unreacted
materials were washed by ethoxyethane (3 9 8 ml). The ethoxyethane was
removed under reduced pressure at room temperature, followed by heating under
high vacuum, to yield a colorless liquid that became more viscous upon extensive
1
drying. Isolated yield was 96 %. H NMR (400 MHz, DMSO-d , d, ppm): 3.86
6
1
23

Synthesis of aryl iodides and azides
NO2
H C
3
N
O
CH
3
Ionic Liquid =
N
N
N
NO2
1
b
I
KI, water
NH2
N2
o
0 C 5-20 min
,
(
1) HCl (1ml)
R1 4a-j
o
0
-5 C, 10 min
N3
(
2) Ionic Liquid
5
-10 min
R1
R1
NaN , water
0 oC, 5-20 min
3
2
a-j
3
R1
5a-j
Scheme 1 Diazotization of anilines using nitrite ionic liquid and synthesis of aryl iodides and aryl azides
(
t, J = 4.8 Hz, 4H, 2CH N), 3.89 (s, 6H, 2CH ), 4.36 (t, J = 4.8 Hz, 4H, 2CH O),
2 3 2
-
1
7
3
.42-7.44 (m, 4H-imidazole), 8.71 (s, 2H, H-2imidazole); IR (KBr, m, cm ): 3,424,
,149, 3,098, 2,970, 1,633, ,1573, 1,452, 1,352, 1,170, 1,129, 845, 759, 653, 621.
Preparation of 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]
ethyl)-1H-imidazol-3-ium dinitrite (1b)
Freshly prepared 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]
ethyl)-1H-imidazol-3-ium dichloride 1a (20 mmol) and NaNO (20 mmol) were
2
added into deionized water (25 ml) and the mixture was stirred for 24 h at room
temperature. The solvent was removed under reduced pressure at 50 °C, to obtain
the crude product containing nitrite ionic liquid and NaCl, which was washed with
acetonitrile (3 9 10 ml). The remaining acetonitrile was removed under high
vacuum to yield yellow transparent liquid that became more viscous upon extensive
1
drying. Isolated yield was 98 %. H NMR (400 MHz, DMSO-d , d, ppm): 3.80 (t,
6
J = 4.8 Hz, 4H, 2CH N), 3.83 (s, 6H, 2CH ), 4.31 (t, J = 4.8 Hz, 4H, 2CH O),
2
2
3
1
3
7
.37–7.39 (m, 4H-imidazole), 8.65 (s, 2H, H-2imidazole); C NMR (125.76 MHz,
DMSO-d ): 36.12 (CH ), 48.97 (CH N), 68.44 (CH O), 123.09 (imi-C), 123.72
6
3
2
2
?
-1
(
imi-C) and 137.58 (NCHN); MS: m/z 328.2 [IL-NO ] ; IR (KBr, m, cm ): 3,443,
2
3
,150, 3,101, 2,553, 1,633, 1,572, 1,331, 1,269, 1,170, 1,129, 828, 759, 649, 620.
General procedures for the conversion of aryl amines to aryl iodides
Aniline derivative (2 mmol) was dissolved in 1 ml of 37 % HCl. The mixture was
stirred at 0–5 °C for 10 min, until the ammonium salt was formed and the aromatic
amine disappeared. The progress of the reaction was monitored by TLC [eluent:
n-hexane/ethyl acetate (80:20)]. Nitrite ionic liquid (1 mmol) was added to the
123

H. Eshghi et al.
aniline solution. The reaction mixture was ground mildly for 5–10 min, the
diazonium salt was formed.
Then, KI (5 mmol, 0.41 g) was added to the mixture and stirring continued for
5
–20 min at room temperature (Table 1). The mixture was filtered and washed with
distilled water (3 9 8 ml) and ethyl acetate (EtOAc, 15 ml). The residue was
extracted with EtOAc (3 9 10 ml) and the combined organic layer was washed
with 10 % aqueous solution of Na SO (15 ml) and then it was dried over
2
3
anhydrous Na SO . The solvent was evaporated to afford aryl iodides.
2
4
General procedures for the conversion of aryl amines to aryl azides
Aniline derivative (2 mmol) was dissolved in 1 ml of 37 % HCl. The mixture was
stirred at 0–5 °C for 10 min, until the ammonium salt was formed and the aromatic
amine disappeared. The progress of the reaction was monitored by TLC [eluent:
n-hexane/ethyl acetate (90:5)]. Nitrite ionic liquid (1 mmol) was added to the
aniline solution. The reaction mixture was ground mildly for 5–10 min, the
diazonium salt was formed. Then, NaN (5 mmol, 0.326 g) was added to the
3
mixture and stirring continued for 6–25 min at room temperature (Table 2). The
mixture was filtered and washed with distilled water (3 9 8 ml) and ethyl acetate
(
EtOAc, 15 ml). The residue was extracted with EtOAc (3 9 10 ml) and the
combined organic layer was washed with 5 % aqueous solution of NaOH (12 ml)
and then it was dried over anhydrous Na SO . The solvent was evaporated to afford
aryl azides.
2
4
Analytical data for selected compounds (Tables 1, 2)
-Iodo-4-nitrobenzene (Table 1, 4a)
1
1
M.p. 170 °C (lit. [19]: 171–172 °C); H NMR (400 MHz, CDCl , d, ppm): 7.98 (d,
3
1
3
J = 7.2 Hz, 2H), 8.08(d, J = 7.2 Hz, 2H); C NMR (125.76 MHz, DMSO-d ):
6
-
1
1
1
04.96, 125.44, 139.20, 147.81; MS: m/z 249.1; IR (KBr, m, cm ): 3,084, 1,594,
,571, 1,512, 1,340, 1,052, 1,008, 837, 734.
1
-Iodo-2-nitrobenzene (Table 1, 4b)
-
1
M.p. 52 °C (lit. [19] 52–53 °C); MS: m/z 248.9; IR (KBr, m, cm ): 3,084, 2,843,
1
,582, 1,567, 1,521, 1,446, 1,333, 1,296, 1,025, 854, 779, 724, 695.
1
-(4-Iodophenyl)ethanone (Table 1, 4h)
1
M.p. 84 °C (lit. [19] 84–85 °C); H NMR (400 MHz, DMSO-d , d, ppm): 2.56 (s,
6
1
H), 7.72 (d, J = 8.8 Hz, 2H), 7.93 (d, J = 8.8 Hz, 2H); C NMR (125.76 MHz,
3
2
DMSO-d ): 27.12, 102.31, 130.40, 136.54, 138.10, 197.99; MS: m/z 245.9; IR (KBr,
6
-
1
m, cm ): 2,962, 2,925, 2,851, 1,668, 1,581, 1,389, 1,264, 1,006, 819, 747, 529.
1
23

Synthesis of aryl iodides and azides
1
-Azido-4-nitrobenzene (Table 2, 5a):
1
Yellow liquid (lit. [43]); H NMR (400 MHz, CDCl , d, ppm): 7.17 (d, J = 8.8 Hz,
3
1
H), 8.27 (d, J = 8.8 Hz, 2H); C NMR (125.76 MHz, DMSO-d ): 119.42, 125.66,
3
2
1
1
6
-
1
44.64, 146.90; MS: m/z 164.1; IR (KBr, m, cm ): 3,072, 2,126, 2,084, 1,605,
,592, 1,516, 1,490, 1,350, 1,289, 1,107, 846, 747, 681, 555.
1
-Azido-2-nitrobenzene (Table 2, 5b)
1
M.p. 129 °C (lit. [43] 129–130 °C); H NMR (400 MHz, CDCl , d, ppm): 7.94 (dd,
3
J = 8.1 Hz, 1H), 7.64 (dt, 1H), 7.35 (dd, J = 7.7 Hz, 1H), 7.27(dt, 1H); MS: m/
-
z 164.1; IR (KBr, m, cm ): 3,035, 2,123, 2,093, 1,604, 1,580, 1,523, 1,478, 1,353,
1
1
,293, 1,172, 857, 775, 742, 703, 637.
1
-(4-Azidophenyl)ethanone (Table 2, 5h)
-
1
M.p. 43 °C (lit. [45] 42–44 °C); MS: m/z 161.1; IR (KBr, m, cm ): 2,929, 2,129,
,093, 1,674, 1,597, 1,507, 1,358, 1,270, 1,181, 963, 831, 722, 583, 542.
2
Results and discussion
Room-temperature ionic liquids (RTILs) have attracted chemists’ interest because
of their particular properties, such as undetectable vapor pressure, wide liquid range,
and the ease of recovery and reuse. RTILs are used as solvents or catalysts in
synthetic organic chemistry [35–39]. Recent advances in ionic liquid research have
provided another route for achieving task-specific ionic liquids (TSILs) in which a
functional group is covalently tethered to the cation or anion of the ionic liquid,
especially to the two N atoms of the imidazole ring. TSILs have been used
increasingly as solvents and reagents or catalysts because of their specific properties
[
37, 38]. We now introduce a new nitrite ionic liquid that can act as a nitrosonium
source for the efficient conversion of aryl amines to their corresponding diazonium
salts. The ionic liquid, 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyl-
oxy] ethyl)-1H-imidazol-3-ium dichloride (1a), was prepared by the efficient
reaction of the 1-methylimidazole with 1-chloro-2-(2-chloroethoxy)ethane at
1
NaNO in deionized water, nitrite ionic liquid (1b) was prepared in 98 % yield
20 °C in 95 % yield. While the resulting ionic liquid was left in contact with
2
(
Scheme 2). It is important to note that this reagent is stable and can be stored for
long periods (months) without significant loss of its activity, and can be readily used
for diazotization of aromatic amines.
The new nitrite ionic liquid was used for the diazotization of aniline derivatives
at 0–5 °C in the presence of HCl. In a model experiment, the mixture of freshly
prepared nitrite ionic liquid and 4-nitroaniline 2a was allowed to come into contact
with 37 % HCl and was stirred for 10 min to obtain the 4-nitrodiazonium
1
intermediate 3a (R = 4-NO ). The 4-nitrodiazonium intermediate was not isolated
and the reaction mixture was added to the solution of potassium iodide to obtain the
2
123

H. Eshghi et al.
aromatic iodide 4a via the well-known Sandmeyer reaction with diazonium
intermediate (Scheme 1). The iodination reaction began immediately after NaI
addition, and the reaction fizzed due to the evolution of nitrogen gas. This one-pot
diazotization–iodination process took 5–20 min to complete. Encouraged by our
initial studies, we then investigated the generality and versatility of this procedure
using a series of structurally different amines (commercially available) under these
optimized conditions. A combinatorial library (parallel format) of aromatic iodides
was smoothly prepared in excellent to moderate yields, and the results are
summarized in Table 1. As indicated in Table 1, the yields of reactions with
electron-rich amines were modest (entries 2i and 2j). Thus, the present method is
especially agreeable for anilines bearing electron-withdrawing groups. Steric effects
of ortho-substituents significantly retarded the reaction rate and decreased the yields
of the corresponding aromatic iodides (entries 2b, 2d, and 2g).
It is known that the co-grinding of dry diazonium nitrate salts with KI results in
the formation of aryl iodides in quantitative yield [40]. However, Kaupp’s method
[
40] requires cumbersome gas phase reagents for the preparation of diazonium salts
and a lengthy reaction time for iodination. Furthermore, neat reactions with dry
diazonium salts may be more dangerous and explosive than wet reactions or those
that take place in solution. Our diazotization–iodination method was safer in this
sense, as the reactions were carried out in a water-paste.
Table 1 Diazotization of aromatic amines by nitrite ionic liquid/HCl in water at 0–5 °C and Iodination
by KI at room temperature
NH2
N2
I
1
0
) HCl (1ml)
-5 C, 10 min
o
KI, water
0 oC, 5-20 min
2
) Ionic Liquid
-10 min
5
R1
R1
R1
2
a-j
3
4a-j
a
b
Entry
Ar–NH
2
(2a–j)
Ar–I (4a–j)
Diazotization/iodination
time (min)
Yield (%)
Ref.
a
b
c
d
e
f
4-NO
2-NO
2
C
C
6
H
H
4
4
NH
2
4-NO
2-NO
2
C
C
6
6
H
4
I
I
10/5
95
88
98
88
85
90
85
95
83
87
[18]
[18]
[20]
[46]
[23]
[23]
[23]
[18]
[18]
[21]
2
6
NH
2
2
H
4
10/15
10/5
4-NCC
6
H
H
4
4
NH
2
2
4-NCC
6
6
H
4
4
I
2-NCC
6
NH
2-NCC
H
I
10/15
10/7
4-BrC
6
H
4
NH
2
4-BrC6H4I
4-ClC
6
6
H
H
4
NH
NH
2
2
4-ClC
2-ClC
6
H
H
4
4
I
I
10/7
g
h
i
2-ClC
4
6
10/15
10/10
10/20
10/20
4-MeCOC
4-MeOC
4-MeC
6
H
4
NH
NH
NH
2
4-MeCOC6H4I
4-MeOC
4-MeC
6
H
4
2
6 4
H I
j
6
H
4
2
6 4
H I
Reaction conditions: 1. Amine a–j (2 mmol), nitrite ionic liquid (1 mmol), HCl (1 ml), H O, 0–5 °C; 2.
2
KI (5 mmol), reaction time (5–20 min), room temperature
a
The products were characterized from their spectral data (IR, 1H NMR), by comparison with reported
samples
b
The yields refer to isolated products
1
23

Synthesis of aryl iodides and azides
Table 2 Diazotization of aromatic amines by nitrite ionic liquid/HCl in water at 0–5 °C and azidation by
NaN
3
at room temperature
NH2
N2
N3
1
0
) HCl (1ml)
-5 C, 10 min
o
NaN , water
3
0 oC, 5-20 min
2
) Ionic Liquid
-10 min
5
R1
R1
R1
2
a-j
3
5a-j
a
b
Entry
Ar–NH
2
(2a–j)
Ar–N
3
(5a–j)
Diazotization/azidation
time (min)
Yield (%)
Ref.
a
b
c
d
e
f
4-NO
2
2
C
6
6
H
4
4
NH
NH
2
4-NO
2-NO
2
C
C
6
H
H
4
4
N
N
3
3
10/10
10/15
10/6
95
90
93
88
85
90
85
95
90
87
[41]
[42]
[41]
[42]
[42]
[41]
[42]
[41]
[34]
[34]
2-NO
C
H
2
2
6
4-NCC
6
6
H
H
4
NH
NH
2
2
4-NCC
6
6
H
4
4
N
N
3
3
2-NCC
4
2-NCC
H
10/15
10/10
10/10
10/15
10/10
10/25
10/20
4-BrC
6
H
4
NH
2
6 4 3
4-BrC H N
4-ClC
6
H
H
4
4
NH
2
2
4-ClC
2-ClC
6
H
H
4
4
N
3
3
g
h
i
2-ClC
6
NH
6
N
4-MeCOC
4-MeOC
4-MeC
6
H
4
NH
NH
NH
2
4-MeCOC
4-MeOC
4-MeC
6 4 3
H N
6
H
4
2
6
H
4
N
3
j
6
H
4
2
6
H
4
N
3
a
Reaction conditions: 1) Amine a–j (2 mmol), nitrite ionic liquid (1 mmol), HCl (1 ml), H
2
O, 0–5 °C;
) NaN (5 mmol), reaction time (6–25 min), room temperature . The products were characterized from
2
their spectral data (IR, 1H NMR), by comparison with reported samples
3
b
The yields refer to isolated products
H C
3
Cl
N
H C
N
N
Cl
DMF
3
O
CH
3
Cl
N
N
Cl
N
O
°
1
20 C, 2h
1
a
Deionized water
4 h, rt
NaNO
2
2
NO2
H C
3
N
O
CH
3
N
N
N
NO2
1
b
Scheme 2 Preparation of nitrite ionic liquid
The present system was further examined for the synthesis of aryl azides with
excellent yield from aryl amines, and the results are summarized in (Table 2, entries
a–j). 4-nitroaniline (2 mmol) was chosen as a model substrate and it was treated
with different molar ratios of nitrite ionic liquid/HCl/NaN . It was observed that a
3
molar ratio of 1/1/5 of nitrite ionic liquid/HCl/NaN and water as solvent were the
3
best at achieving the highest yield of the product as indicated in Table 2.
Various aromatic amines, with electron-withdrawing groups as well as electron-
donating groups, were transformed into aryl azides in excellent yields (Table 2).
123

H. Eshghi et al.
This result is in agreement with reported methods on diazotization–azidation of
aniline [41, 42]. All the well-known products were characterized by comparing their
1
13
H, C NMR, Mass and IR) spectroscopic data with the literature values.
(
Compared with the traditional methods, the quantitative conversion without any
by-products and the stability of nitrite ionic liquid in comparison with HNO is an
2
attractive property of the new nitrite ionic liquid as a nitrosonium source [43, 44].
Furthermore, avoiding the use of toxic reagents make this process attractive from
the standpoint of the environment. In the present study, we investigated whether IL-
Cl (1a) can be recycled. After removal of the mixture of product, possible
impurities, and unreacted materials, the remaining IL-Cl (1a) was reused for the
preparation of IL-NO (1b) without significant loss in its efficiency.
2
Conclusion
In conclusion, we have introduced a method for an easy preparation of nitrite ionic
liquid as a nitrosonium ion which affords an attractive, practical, and clean
diazotization of aniline derivatives. Also, we have developed a mild, one-pot
synthetic method for the preparation of aryl iodides and aryl azides from amines in
the presence of nitrite ionic liquid using HCl in water. The advantages are excellent
yields, easy and clean workup, extremely fast reaction, high chemoselectivity, and
operation at room temperature.
Acknowledgment We are grateful to department of chemistry, Ferdowsi University of Mashhad, for
financial support (Grant no. 3/15592).
References
1
2
3
4
5
6
. J. Masllorens, S. Bouquillon, A. Roglans, F. H e´ nin, J. Muzart, J. Organomet. Chem. 690, 3822 (2005)
. S. Sengupta, S. Bhattacharyya, J. Chem. Soc. Perkin Trans. 1, 1943 (1993)
. S. Sengupta, S. Bhattacharyya, Tetrahedron Lett. 36, 4475 (1995)
. R. Glaser, C.J. Horan, J. Org. Chem. 60, 7518 (1995)
. R. Glaser, C.J. Horan, H. Zollinger, Angew. Chem. Int. Ed. 36, 2210 (1997)
. V. Farina, E.W. Abel, F.G.A. Stone, G. Wilkinson, Comprehensive Organometallic Chemistry II, vol.
12 (Pergamon, Oxford, 1995).
7. A. deMeijere, F.E. Meyer, Angew. Chem. Int. Ed. Engl. 33, 2379 (1995)
8. J.J. Li, G.W. Gribble, Tetrahedron Organic Chemistry Series, vol. 20 (Pergamon, Amsterdam, 2000).
9. B.C.G. Soderberg, Coord. Chem. Rev. 248, 1085 (2004)
1
1
1
1
1
1
1
1
1
1
0. D. Prajapati, M. Gohain, Tetrahedron 60, 815 (2004)
1. J.G. deVries, Can. J. Chem. 79, 1086 (2001)
2. L. Liu, Y. Zhang, B. Xin, J. Org. Chem. 71, 3994 (2006)
3. H.H. Hodgson, Chem. Rev. 40, 251 (1947)
4. H. Zollinger, Azo and Diazo Chemistry (Interscience, New York, 1961)
5. S. Patai, The Chemistry of Diazonium and Diazo Groups (Wiley, New York, 1978)
6. C. Galli, Chem. Rev. 88, 765 (1988)
7. W. Baik, W. Luan, H.J. Lee, C.H. Yoon, S. Koo, B.H. Kim, Can. J. Chem. 83, 213 (2005)
8. E.A. Krasnokutskaya, N.I. Semenischeva, V.D. Filimonov, P. Knochel, Synthesis 39, 81 (2007)
9. V.D. Filimonov, N.I. Semenischeva, E.A. Krasnokutskaya, A.N. Tretyakov, H.Y. Hwang, K.W. Chi,
Synthesis 40, 185 (2008)
1
23

Synthesis of aryl iodides and azides
20. D.A. Gorlushko, V.D. Filimonov, E.A. Krasnokutskaya, N.I. Semenischeva, B.S. Go, H.Y. Hwang,
E.H. Cha, KWh Chi, Tetrahedron Lett. 49, 1080 (2008)
21. M.E. Trusova, E.A. Krasnokutskaya, P.S. Postnikov, Y. Choi, K.W. Chi, V.D. Filimonov, Synthesis
43, 2154 (2011)
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
2. A. Zarei, A.R. Hajipour, L. Khazdooz, Synthesis 41, 941 (2009)
3. F. Nemati, A. Elhampour, Sci. Iran. C 19, 1594 (2012)
4. E.F.V. Scriven, K. Turnbull, Chem. Rev. 88, 297 (1988)
5. F. Avemaria, V. Zimmermann, S. Braese, Synlett 15, 1163 (2004)
6. A.L. Shaikh, V.G. Puranik, A.R. Deshmukh, Tetrahedron Lett. 47, 5993 (2006)
7. C.A. Gartner, Curr. Med. Chem. 10, 671 (2003)
8. M. Kuse, I. Doi, N. Kondo, Y. Kageyama, M. Isobe, Tetrahedron 61, 5754 (2005)
9. S.Y. Han, S.S. Park, W.G. Lee, Y.K. Min, B.T. Kim, Bioorg. Med. Chem. Lett. 16, 129 (2006)
0. M.S. Rizk, X. Shi, M.S. Platz, Biochemistry 45, 543 (2006)
1. J. Das, S.N. Patil, R. Awasthi, C.P. Narasimhulu, S.Trehan, Synthesis 37, 1801 (2005)
2. Q. Liu, Y. Tor, Org. Lett. 5, 2571 (2003)
3. W. Zhu, D. Ma, Chem. Commun. 7, 888 (2004)
4. C.Z. Tao, X. Cui, J. Li, A.X. Liu, L. Liu, Q.X. Guo, Tetrahedron Lett. 48, 3525 (2007)
5. K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, Dyes Pigment. 80, 30 (2009)
6. M. Ghasemzadeh, Synlett 22, 1331 (2011)
7. C. Yue, A. Mao, Y. Wei, M. Lu, Catal. Commun. 9, 1571 (2008)
8. H. Eshghi, M. Bakavoli, M. Ghasemzadeh, S.M. Seyedi, Res. Chem. Intermed (2013). doi:10.1007/
s11164-013-1302-1
39. D.R. Macfarlane, J.M. Pringle, K.M. Johansson, S.A. Forsyth, M. Forsyth, Chem. Commun. 18, 1905
(2006)
4
4
4
4
4
4
4
0. G. Kaupp, A. Herrmann, J. Schmeyers, Chem. Eur. J. 8, 1395 (2002)
1. K. Barral, A.D. Moorhouse, J.E. Moses, Org. Lett. 9, 1809 (2007)
2. M.A. Karimi Zarchi, N. Ebrahimi, J. Appl. Polym. Sci. 121, 2621 (2011)
3. F. Nemati, A. Elhampour, J. Chem. Sci. 124, 889 (2012)
4. M.A. Karimi Zarchi, R. Nabaei, S. Barani, J. Appl. Polym. Sci. 123, 788 (2012)
5. J.T.B. Kueh, K.W. Choia, M.A. Brimble, Org. Biomol. Chem. 10, 5993 (2012)
6. Sigma-Aldrich Corporation. Aldrich Handbook of Fine Chemicals and Laboratory Equipment
(Aldrich: Milwaukee, 2006–2007)
123