An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions

Article abstract of DOI:10.1134/S1070428020090225

Abstract: A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.

Full text of DOI:10.1134/S1070428020090225

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 9, pp. 1640–1645. © Pleiades Publishing, Ltd., 2020.
An Efficient Synthesis of Nitriles from Aldoximes in the Presence
of Trifluoromethanesulfonic Anhydride in Mild Conditions
N. Uludaga,*
a Universirty of Namık Kemal, Faculty of Art and Sciences, Department of Chemistry, Tekirdag, 59030 Turkey
e-mail: nuludag@nku.edu.tr
Received March 26, 2020; revised April 4, 2020; accepted April 16, 2020
Abstract—A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles
using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes,
including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding
nitriles in good to excellent yields.
Keywords: aldoximes, nitriles, trifluoromethanesulfonic anhydride, dehydration
DOI: 10.1134/S1070428020090225
INTRODUCTION
azol-1-yl 4-methylbenzenesulfonate (Bt-OTs) [28],
P(RNCH2CH2)3N (proazaphosphatranes) [29], silica-
supported thionyl chloride [30], N-hydroxyphthalimide
[31], and (COCl)2 [32]. However, these reagents may
have some limitations, including their high cost, scar-
city, low yields, harsh reaction conditions, long reac-
tion times, and work-up difficulties. Therefore, there is
still a need to develop a better method for synthesizing
nitriles.
Substituted nitriles are key molecular scaffolds in
the synthesis of many organic compounds [1–3].
Several routes for the synthesis of nitriles from aldox-
imes are important because nitriles are useful organic
synthons in preparative organic chemistry; they can be
converted into aldehydes, amides, ketones, carboxylic
acids, and nitrogen-containing heterocycles [4, 5]. Yet
the search for better reagents continues, generating
interest methods for converting aldoximes to nitriles.
Although many transformations have been reported
[6–15], the development of more efficient methods for
synthesizing nitriles remains a goal of the scientific
community [16, 17].
Trifluoromethanesulfonic anhydride was introduced
for the use in synthesizing primary amides and their
conversion into nitriles [33], although it has also been
used in other important organic reactions [34, 35]. Our
interest in nitrile chemistry led us to consider the use of
triflic anhydride as an alternative for the efficient
synthesis of nitriles from aldoximes in mild reaction
conditions (e.g., in tetrahydrofuran at 0–5°C). This
method leads to the efficient manipulation of complex
functional groups in a reasonable and sustainable
chemical pathway. For example, aldoximes can be
converted into nitriles using triflic anhydride and
triethylamine in THF (Scheme 1). Thus, aldoximes
were prepared using the procedure reported in the
literature [26] and, herein, the development of a simple
process that can be used to dehydrate aldoximes in
a short time is reported.
Nitriles are the key constituents of many pharmaco-
phores in commercially available drugs [18], and
nitrile-containing pharmaceuticals have diverse medic-
inal indications. For example, entacopone is a vinylic
nitrile prescribed for Parkinson’s disease [19], and
finrozole is an approved drug used as a novel non-
steroidal inhibitor for the treatment of breast cancer
[20]. The role of nitriles in synthetic chemistry high-
lights the importance of developing a fast, low-cost,
facile, and feasible method for synthesizing various
nitriles. A variety of techniques have been developed to
synthesize nitriles from diverse aldoxime precursors
[21–25]. Numerous reagents have been developed for
this purpose, including FeCl3 [26], Na2SO3/SOCl2 [27],
(1H-benzotriazol-1-yloxy)tris(dimethylamino)phos-
phonium hexafluorophosphate (BOP), 1H-benzotri-
RESULTS AND DISCUSSION
The reactions were conducted at temperatures rang-
ing from 0 to 5°C. As shown in Table 1, satisfactory
1640

AN EFFICIENT SYNTHESIS OF NITRILES FROM ALDOXIMES
1641
Scheme 1.
into nitriles provided excellent yields. The products
1
were characterized by H and 13C NMR, IR, and mass
(CF3SO2)2O
THF, Et3N, 0–5°C
spectra.
R
CN
R
NOH
1–23
EXPERIMENTAL
R = aryl, heteroaryl, cycloalkyl, alkyl, allyl (see Table 1).
The IR spectra were recorded using a Mattson FT-
1
IR spectrometer. The H and 13C NMR spectra were
results were attained in a short reaction time [36–38].
By optimizing the reaction conditions, a 98% yield of
nitrile was obtained in a minimum reaction time
(Table 1, entry no. 1). The experimental procedure was
then extended for the one-pot synthesis of nitriles in
a simple and straightforward way that generally pro-
vided good yields. Thus, different aldoximes, including
aromatic, heteroaromatic, aliphatic, and cycloaliphatic
ones, were converted successfully into the correspond-
ing nitriles under optimized conditions. Scheme 2
shows a plausible mechanism of dehydration of
aldoximes by the action of trifluoromethanesulfonic
anhydride and triethylamine. The described reaction is
simpler and faster than the reported ones, and the dehy-
dration method used for converting various aldoximes
recorded on a Bruker 400 spectrometer (400 MHz
for H) in CDCl3 at 25°C; the chemical shifts were
1
measured relative to the residual proton and carbon
signals of the solvent. The melting points were
measured in capillary tubes on an Electrothermal IA
9000 apparatus and are uncorrected. The mass spectra
(electron impact, 70 eV) were recorded on a Shimadzu
GCMS-QP2010 Ultra spectrometer. Column chroma-
tography was performed using 60–120 mesh silica gel,
and the reactions were monitored by thin-layer chroma-
tography on silica gel 60 F254 plates. All chemicals
and solvents were purchased from commercial sources.
The solvents were purified according to standard
methods.
Table 1. Synthesis of nitriles from aldoximes in the presence of trifluoromethanesulfonic anhydride and triethylamine
Compound no.
R
Reaction time, h
Yield, %
98
1
2
Ph
1.5
3.5
2.5
2.5
3
4-FC6H4
79
3
4-BrC6H4
94
4
4-ClC6H4
91
5
4-F3CC6H4
4-O2NC6H4
3-O2NC6H4
4-MeC6H4
86
6
1
88
7
1.5
2
84
8
91
9
3-MeC6H4
2.5
1
89
10
11
12
13
14
15
16
17
18
19
20
21
22
23
4-HOC6H4
4-MeOC6H4
3-MeOC6H4
4-Me2NC6H4
(E)-PhCH=CH
cyclo-C6H11
C6H13
94
2.5
3
96
93
2
87
0.5
1.5
2.5
1
91
68
56
Pyridin-2-yl
Pyridin-3-yl
Naphthalen-1-yl
Naphthalen-2-yl
Furan-3-yl
88
1.5
2.5
2.5
1.5
2
91
94
96
87
Thiophen-2-yl
1H-Indol-3-yl
92
3.5
79
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020

ULUDAG
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Scheme 2.
O
O
S
O
S
R
N
S
OH
+
F3C
O
CF3
+
F3CSO2O–
N
R
O
CF3
–F3CSO2O–
R
N
O
O
O
H
Et3N
General procedure for dehydration of aldoximes
into nitriles. Triethylamine (3.0 mmol) was added to
a stirred mixture of aldoxime (1.5 mmol) and 10 mL
of THF, and trifluoromethanesulfonic anhydride
(3.0 mmol) was then added. The mixture was stirred at
0°C for a time indicated in Table 1, and the progress of
the reaction was monitored by TLC (ethyl acetate–
hexane, 6:1). After completion of the reaction, the mix-
ture was poured into water, neutralized with a 10% so-
lution of NaHCO3 (20 mL), and extracted with ethyl
acetate (3×10 mL). The combined extracts were dried
over anhydrous Na2SO4 and concentrated, and the
residue was purified by column chromatography on
silica gel (60–120 mesh) using ethyl acetate–petroleum
ether (2:1) as eluent.
4-(Trifluoromethyl)benzonitrile (5). Yield
220 mg, oil, Rf = 0.44 (EtOAc) [39]. IR spectrum
(KBr), ν, cm–1: 2935, 2238 (CN), 1751, 1283, 1172,
1
841. H NMR spectrum δ, ppm: 7.72 d (2H, J =
8.2 Hz), 7.81 d (2H, J = 8.2 Hz). 13C NMR spectrum,
δC, ppm: 116.0, 117.4, 122.8, 125.1, 1323.4, 133.5.
Mass spectrum, m/z (Irel, %): 172 (12) [M + 1]+, 171
(100) [M]+, 121 (83).
4-Nitrobenzonitrile (6). Yield 217 mg, white solid,
mp 146–147°C, Rf = 0.47 (EtOAc) [42]. IR spectrum
(KBr), ν, cm–1: 3081, 2877, 2239 (CN), 1611, 1538,
1341, 816. 1H NMR spectrum, δ, ppm: 7.91 d (2H, J =
9.0 Hz). 8.31 d (2H, J = 9.0 Hz). 13C NMR spectrum,
δC, ppm: 115.6, 118.7, 123.8, 133.1, 149.6. Mass spec-
trum, m/z (Irel, %): 148 (72) [M + 1]+, 132 (7), 118 (71),
102 (100), 90 (29), 75 (36), 63 (11), 51 (18).
Benzonitrile (1). Yield 154 mg, colorless oil, Rf =
0.53 (EtOAc) [39]. IR spectrum (KBr), ν, cm–1: 3055,
3-Nitrobenzonitrile (7). Yield 184 mg, solid,
mp 114–115°C, Rf = 0.53 (EtOAc) [15, 43]. IR spec-
trum (KBr), ν, cm–1: 3078, 2865, 2241 (CN), 1612,
1
2220 (CN), 1488, 1441. H NMR spectrum δ, ppm:
7.51–7.43 m (2H), 7.62–7.56 m (1H), 7.67–7.63 m
(2H). 13C NMR spectrum, δC, ppm: 112.5, 118.9,
129.1, 133.1, 132.8. Mass spectrum, m/z (Irel, %): 103
(100) [M]+, 76 (15).
1
1521, 1378, 814. H NMR spectrum, δ, ppm: 8.41 d
(2H, J = 9.1 Hz), 8.02 s (1H), 7.76 s (1H). 13C NMR
spectrum, δC, ppm: 114.8, 115.6, 127.1, 127.9, 131.5,
136.8, 144.1. Mass spectrum, m/z (Irel, %): 148 (34)
[M]+, 102 (100).
4-Fluorobenzonitrile (2). Yield 143 mg, oil, Rf =
0.45 (EtOAc) [40]. IR spectrum (KBr), ν, cm–1: 3071,
1
2235 (CN), 1481, 752. H NMR spectrum, δ, ppm:
4-Methylbenzonitrile (8). Yield 159 mg, oil, Rf =
0.56 (EtOAc) [39]. IR spectrum (KBr), ν, cm–1: 3021,
2950, 2863, 2228 (CN), 1919, 1701, 1603, 1511, 1450,
7.11–7.22 m (2H), 7.53–7.62 m (2H). 13C NMR spec-
trum, δC, ppm: 108.3, 116.3, 117.9, 134.3, 165.1. Mass
spectrum: m/z (Irel, %): 122 (7) [M + 1]+, 121 (100)
[M]+, 94 (31).
1
1210, 1177, 1120, 1041, 817. H NMR spectrum, δ,
ppm: 2.43 s (3H), 7.27 d (2H, J = 8.1 Hz), 7.44 d (2H,
J = 8.1 Hz). 13C NMR spectrum, δC, ppm: 21.7, 108.4,
119.5, 128.8, 132.6, 144.3. Mass spectrum, m/z
(Irel, %): 118 (14) [M + 1]+, 117 (100) [M]+, 116 (71).
4-Bromobenzonitrile (3). Yield 271 mg, solid,
mp 111–113°C, Rf = 0.43 (EtOAc) [39]. IR spectrum
(KBr), ν, cm–1: 3081, 2215 (CN), 1578, 1451, 1061,
1
832. H NMR spectrum, δ, ppm: 7.48 d (2H, J =
3-Methylbenzonitrile (9). Yield 105 mg, oil, Rf =
0.55 (EtOAc) [39]. IR spectrum (KBr), ν, cm–1: 2998,
7.8 Hz), 7.61 d (2H, J = 7.8 Hz). 13C NMR spectrum,
δC, ppm: 110.3, 119.3, 129.0, 131.7, 132.3. Mass spec-
trum: m/z (Irel, %): 183 (61) 181 (72) [M]+, 102 (100).
1
2231 (CN), 1773, 1234, 781, 683. H NMR spectrum,
δ, ppm: 7.33 t (1H, J = 7.4 Hz), 7.39–7.43 m (3H).
13C NMR spectrum, δC, ppm: 22.1, 111.3, 118.1, 129.0,
129.8, 131.1, 134.7, 138.3.
4-Chlorobenzonitrile (4). Yield 205 mg, solid,
mp 92–94°C, Rf = 0.51 (EtOAc ) [41]. IR spectrum
(KBr), ν, cm–1: 2938, 2241 (CN), 1281, 1117, 778.
1H NMR spectrum, δ, ppm: 7.42 d (2H, J = 8.1 Hz),
7.63 d (2H, J = 8.5 Hz). 13C NMR spectrum, δC, ppm:
110.3, 118.7, 128.4, 134.3, 138.5. Mass spectrum,
m/z (Irel, %): 137 (100) [M]+, 102 (41).
4-Hydroxybenzonitrile (10). Yield 167 mg, solid,
mp 107–109°C, Rf = 0.51 (EtOAc) [39]. IR spectrum
(KBr), ν, cm–1: 3380, 2251 (CN), 1601, 1574, 1432,
1
1364, 830. H NMR spectrum, δ, ppm: 6.95 d (3H,
H
arom, OH, J = 8.3 Hz), 7.53 d (2H, J = 8.3 Hz).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020

AN EFFICIENT SYNTHESIS OF NITRILES FROM ALDOXIMES
1643
1
13C NMR spectrum, δC, ppm: 103.1, 176.5, 118.3,
133.5, 164.1. Mass spectrum: m/z (Irel, %): 120 (14)
[M + 1]+, 119 (100) [M]+, 91 (21). Found, %: C 70.65;
H 4.28; N 11.67. C7H5NO. Calculated, %: C 70.58;
H 4.23; N 11.76.
2246 (CN), 1453, 1182. H NMR spectrum δ, ppm:
0.93 t (3H, J = 7.3 Hz), 1.31–1.48 m (4H), 1.61–1.73 m
(2H), 2.35 t (4H, J = 7.4 Hz). 13C NMR spectrum, δC,
ppm: 13.7, 17.4, 22.2, 25.4, 30.7, 120.1. Mass spec-
trum, m/z (Irel, %): 99 (10) [M + 1]+, 81 (60), 55 (30).
4-Methoxybenzonitrile (11). Yield 191 mg, white
solid, mp 55–57°C, Rf = 0.44 (EtOAc) [15]. IR spec-
trum (KBr), ν, cm–1: 3025, 2942, 2843, 2561, 2218
Pyridine-2-carbonitrile (17). Yield 132 mg,
colorless oil, Rf = 0.55 (EtOAc) [39]. IR spectrum
(KBr), ν, cm–1: 3048, 2913, 2233 (CN), 1673, 1651,
1
1
(CN), 1606, 1509, 1305, 1258, 1024, 830. H NMR
1576, 1451, 1435, 1360, 1293, 990, 782. H NMR
spectrum, δ, ppm: 3.91 s (3H, OCH3), 6.96 d (2H, J =
9.0 Hz), 7.61 d (2H, J = 8.2 Hz). 13C NMR spectrum,
δC, ppm: 56.5, 103.3, 113.9, 119.7, 132.8, 165.3. Mass
spectrum, m/z (Irel, %): 134 (9) [M + 1]+, 133 (100)
[M]+, 102 (60).
spectrum, δ, ppm: 7.62 s (1H), 7.73 s (1H), 7.96 s (1H),
8.73 s (1H). 13C NMR spectrum, δC, ppm: 118.3, 127.5,
127.1, 133.1, 136.3, 152.1. Mass spectrum, m/z
(Irel, %): 104 (100) [M]+, 77 (30), 51 (15).
Pyridine-3-carbonitrile (18). Yield 142 mg, white
solid, mp 50–52°C, Rf = 0.44 (EtOAc) [48, 49].
IR spectrum (KBr), ν, cm–1: 3014, 2927, 2239 (CN),
1671, 1644, 1618, 1433, 1430, 1353, 1289, 997.
1H NMR spectrum, δ, ppm: 7.44 d.d.d (1H, J = 7.7,
4.5, 0.8 Hz), 7.93 d.t (1H, J = 7.8, 1.8 Hz), 8.82 d.d
(1H, J = 4.7, 1.6 Hz), 8.86 d (1H, J = 1.3 Hz).
13C NMR spectrum, δC, ppm: 111.4, 113.7, 123.1,
138.4, 153.7, 154.1. Mass spectrum, m/z (Irel, %): 105
(20) [M + 1]+, 77 (60), 51 (20).
3-Methoxybenzonitrile (12). Yield 185 mg, oil,
Rf = 0.42 (EtOAc) [44]. IR spectrum (KBr), ν, cm–1:
2945, 2235 (CN), 1593, 1291, 1263, 1041, 779, 683.
1H NMR spectrum, δ, ppm: 3.81 s (3H, OCH3), 7.14–
7.31 m (4H). 13C NMR spectrum, δC, ppm: 55.9, 114.1,
116.2, 118.6, 119.3, 123.8, 130.2, 159.6. Mass spec-
trum, m/z (Irel, %): 134 (11) [M + 1]+, 133 (100) [M]+,
105 (60), 104 (100).
4-(Dimethylamino)benzonitrile (13). Yield
219 mg, solid, mp 72–74°C, Rf = 0.48 (EtOAc) [39].
IR spectrum (KBr), ν, cm–1: 2901, 2844, 2823, 2218
(CN), 1608, 1578, 1432, 1368, 844. 1H NMR spectrum,
δ, ppm: 3.02 s [6H, (CH3)2N], 6.68 d (2H, J = 9.0 Hz),
7.43 d (2H, J = 9.0 Hz). 13C NMR spectrum, δC,
ppm: 97.3, 111.3, 121.5, 132.9, 154.2. Mass spec-
trum, m/z (Irel, %): 146 (68) [M]+, 131 (26), 116 (4),
102 (14), 91 (4).
Naphthalene-1-carbonitrile (19). Yield 215 mg,
oil, Rf·= 0.38 (EtOAc) [39]. IR spectrum (KBr), ν,
cm–1: 3060, 2227 (CN), 1686, 1591, 1512, 1394, 1341,
801, 771, 451. 1H NMR spectrum, δ, ppm: 8.22 d (1H,
J = 8.3 Hz), 8.07 d (1H, J = 7.9 Hz), 7.88 t (2H, J =
7.8 Hz), 7.60 s (1H), 7.57 s (1H), 7.44 s (1H).
13C NMR spectrum, δC, ppm: 134.2, 133.9, 131.7,
131.3, 128.8, 128.3, 126.4, 125.6, 124.0, 117.6, 111.5.
Mass spectrum, m/z (Irel, %): 154 (15) [M + 1]+, 152
(100), 125 (20), 76 (15).
(E)-3-Phenylprop-2-enenitrile (14). Yield 193 mg,
colorless oil, Rf = 0.51 (EtOAc) [45]. IR spectrum
(KBr), ν, cm–1: 2928, 2228 (CN), 1629, 1441, 854.
1H NMR spectrum δ, ppm: 5.83 d (1H, =CHCN, J =
16.1 Hz), 7.38–7.51 m. 13C NMR spectrum, δC, ppm:
96.5, 118.3, 127.4, 128.2, 131.4, 133.7, 151.5. Mass
spectrum, m/z (Irel, %): 130 (11) [M + 1]+, 129 (100),
102 (65). Found, %: C 83.76; H 5.37; N 10.88. C9H7N.
Calculated, %: C 83.69; H 5.46; N 10.84.
Naphthalene-2-carbonitrile (20). Yield 219 mg,
white solid, mp 66–68°C, Rf = 0.41 (EtOAc) [46].
IR spectrum (KBr), ν, cm–1: 3058, 2229 (CN), 1592,
1501, 1282, 963, 817, 752. 1H NMR spectrum, δ, ppm:
7.57–7.69 m (3H), 7.89–7.96 m (3H), 8.21 s (1H).
13C NMR spectrum, δC, ppm: 108.6, 119.7, 126.5,
127.3, 128.1, 128.3, 129.0, 129.7, 131.5, 133.7, 133.5.
Mass spectrum, m/z (Irel, %): 154 (11) [M + 1]+, 152
(100), 125 (20).
Cyclohexanecarbonitrile (15). Yield 111 mg,
colorless oil, Rf = 0.51 (EtOAc) [46]. IR spectrum
1
(KBr): ν 2234 cm–1 (CN). H NMR spectrum, δ, ppm:
Furan-3-carbonitrile (21). Yield 121 mg, solid,
mp 28–30°C, Rf = 0.41 (EtOAc) [49, 50]. IR spectrum
(KBr), ν, cm–1: 2934, 2242 (CN), 1651, 1093. 1H NMR
spectrum δ, ppm: 6.57 s (1H), 6.87 s, 7.63 s (1H).
13C NMR spectrum, δC, ppm: 112.0, 118.7, 119.5,
136.2, 145.3. Mass spectrum, m/z (Irel, %): 94 (18)
[M + 1]+, 67 (100).
1.53–1.38 m (4H), 1.79–1.64 m ( 4H), 1.81–1.87 m
(2H), 2.63 t.t (1H, J = 8.2, 3.8 Hz). 13C NMR spectrum,
δC, ppm: 24.7, 25.4, 28.7, 29.5, 122.6. Mass spectrum,
m/z (Irel, %): 110 (22) [M + 1]+, 98 (35), 85 (100).
Hexanenitrile (16). Yield 81 mg, colorless oil, Rf =
0.38 (EtOAc) [47]. IR spectrum (KBr), ν, cm–1: 2926,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020

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1644
10. Wang, E.C., Huang, K.S., Chen, H.M., Wu, C.C., and
Thiophene-2-carbonitrile (22). Yield 150 mg,
Lin, G.J., J. Chin. Chem. Soc., 2004, vol. 51, p. 619.
https://doi.org/10.1002/jccs.200400093
11. Ghos, P., Saha, B., Pariyar, G.C., and Tamang, A.,
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https://doi.org/10.1016/j.tetlet.2016.06.125
12. Chill, S.T. and Mebane, R.C., Synth. Commun., 2009,
vol. 39, p. 3601.
colorless oil, Rf = 0.48 (EtOAc) [39]. IR spectrum
1
(KBr), ν, cm–1: 3051, 2934, 1236. H NMR spectrum,
δ, ppm: 7.14 d.d (1H, J = 5.6, 3.8 Hz), 7.60 d.d (1H,
J = 5.3, 1.3 Hz), 7.62–7.64 m (1H). 13C NMR spec-
trum, δC, ppm: 110.1, 114.6, 127.1, 133.7, 136.4. Mass
spectrum, m/z (Irel, %): 110 (12) [M + 1]+, 83 (80).
Indole-3-carbonitrile (23). Yield 168 mg, solid,
mp 178–180°C, Rf = 0.52 (EtOAc) [30]. IR spectrum
(KBr), ν, cm–1: 3012, 292, 2241. 1H NMR spectrum, δ,
ppm: 7.21–7.82 m (5H), 8.81 s (NH). 13C NMR spec-
trum, δC, ppm: 81.3, 116.3, 125.5, 126.3, 127.1, 127.3,
128.4, 129.7, 133.1. Mass spectrum, m/z (Irel, %): 143
(25) [M + 1]+, 116 (100).
https://doi.org/10.1080/00397910902788174
13. Reddy, K.R., Maheswari, U., Venkateshwar, M.,
Prashanti, S., and Kantam, M.L., Tetrahedron Lett.,
2009, vol. 50, p. 2050.
https://doi.org/10.1016/j.tetlet.2009.02.057
14. Kalkhambkar, R.G., Bunge, S., and Laali, K.K., Tetra-
hedron Lett., 2011, vol. 52, p. 5184.
https://doi.org/10.1016/j.tetlet.2011.07.135
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Rubtsov, A.E., and Malkov, A.V., Org. Lett., 2018,
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FUNDING
The study was performed under financial support by
the Namık Kemal University Scientific Research Projects
Coordination Department (project no. NKUBAP.00.10.
YL.14.06).
https://doi.org/10.1021/acs.orglett.7b03862
16. Shu, Z., Ye, Y., Deng, Y., Zhang, Y., and Wang, J.,
Angew. Chem., Int. Ed., 2013, vol. 52, p. 10573.
https://doi.org/10.1002/anie.201305731
17. Anbarasan, P., Neumann, H., and Beller, M., Angew.
Chem., Int. Ed., 2011, vol. 50, p. 519.
https://doi.org/10.1002/anie.201006044
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CONFLICT OF INTEREST
No conflict of interest was declared by the author.
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