Synthesis and antimicrobial evaluation of substituted (1,1'-biphenyl)-4-yl(3-methylbenzofuran-2-yl)methanones by Suzuki cross-coupling reaction

Article abstract of DOI:10.1134/S1070363216120410

A series of new substituted [1,1'-biphenyl]-4-yl(3-methylbenzofuran-2-yl)methanones was prepared by Suzuki cross-coupling from (4-bromophenyl)(3-methylbenzofuran-2-yl)methanone. The obtained compounds were assayed for their in vitro antibacterial activity against different types of bacterial strains; antifungal activity was also examined by inhibitory effect against different fungal strains.

Full text of DOI:10.1134/S1070363216120410

ISSN 1070-3632, Russian Journal of General Chemistry, 2016, Vol. 86, No. 12, pp. 2791–2796. © Pleiades Publishing, Ltd., 2016.
Synthesis and Antimicrobial Evaluation of Substituted
(1,1'-Biphenyl)-4-yl(3-methylbenzofuran-2-yl)methanones
by Suzuki Cross-Coupling Reaction1
B. J. Reddy and V. P. Reddy*
Department of Chemistry, Osmania University, Telangana, Hyderabad, 500007 India
*e-mail: bonamjagadeeshreddy@gmail.com
Received May 11, 2016
Abstract—A series of new substituted [1,1'-biphenyl]-4-yl(3-methylbenzofuran-2-yl)methanones was prepared
by Suzuki cross-coupling from (4-bromophenyl)(3-methylbenzofuran-2-yl)methanone. The obtained compounds
were assayed for their in vitro antibacterial activity against different types of bacterial strains; antifungal
activity was also examined by inhibitory effect against different fungal strains.
Keywords: benzofuran, Suzuki cross-coupling, antimicrobial activity
DOI: 10.1134/S1070363216120410
Benzofuran-containing compounds [1] are ubi-
quitous in nature, particularly among plants. Often
such natural products possessing benzofuran core are
endowed with useful pharmacological properties. This
has generated enormous interest in synthetic products
containing benzofuran moiety and has resulted in
active development of benzofuran chemistry during
last several years. Recent reviews showed that benzo-
furan [2] is clinically potent moiety possessing diverse
biological activities and profound efficacy. Benzofuran
derivatives possess a wide range of biological activitiy
such as antimicrobial [3–5], antitumor [6, 7], anti-
inflammatory [8], antibacterial [9], antifungal [10],
antidepressant [11], analgesic [12], and hypoglycemic
[13].
[18–21]. The most suitable catalyst for Suzuki-
Miyaura coupling is Pd(PPh3)4 because of its tolerance
to the functional groups and low sensitivity towards
water and air, so that the reactions can take place even
in aqueous medium [22].
Therefore being inspired with the potential bio-
activity of benzofuran and biaryl moieties, we have
undertaken the synthesis of some new benzofuran–
biaryl derivatives using Suzuki cross-coupling reac-
tion. All the synthesized compounds have been tested
in vitro for their antibacterial and antifungal activities.
Synthesis of new benzofuran derivatives 5a–5i was
carried out according to Scheme 1. The carbon–carbon
bond was formed by reacting (4-bromophenyl)(3-
methylbenzofuran-2-yl)methanone [23] with various
arylboronic acids 4a–4i with the formation of target
compounds [1,1'-biphenyl]-4-yl(3-methylbenzofuran-
2-yl)methanones 5a–5i (Table 1).
Aryl–aryl and aryl–vinyl bonds formation is very
important in organic synthesis and has a wide range of
applications of industrial interest, including synthesis
of pharmaceuticals, polymers, herbicides, and the other
materials [14, 15]. Some natural biaryl derivatives can
be used as drugs and an example of this is Mastigo-
phorene A [16]. The palladium-catalyzed reaction
between organoboron compounds and organic halides
that led to the formation of carbon–carbon bond has
been first reported by Akira Suzuki and Miyayura and
it was a revolution in organic couplings [17]. For the
synthesis of biaryl compounds, palladium-catalyzed
Suzuki-Miyaura coupling is the most attractive method
The proposed structure for compound 5a was
confirmed by the spectral data as [1,1'-biphenyl]-4-yl-
(3-methylbenzofuran-2-yl)methanone. In the IR spec-
trum of 5a, the peaks at 1077 and 1749 cm–1 confirmed
the presence of C–O–C motif and carbonyl groups
1
respectively. In H NMR spectrum of 5a a singlet at
δ = 2.68 ppm corresponding to the resonance of CH3
protons was registered. In 13C NMR spectrum of the
discussed compound a signal δ 10.08 ppm cor-
responding to the methyl carbon resonance and another
signal at δ = 185.4 ppm corresponding to resonance of
1 The text was submitted by the authors in English.
2791

2792
B.J. REDDY, V.P. REDDY
Scheme 1. Synthesis of substituted [1,1'-biphenyl]-4-yl(3-methylbenzofuran-2-yl)methanones.
Br
Br
O
OH
O
O
K2CO3, reflux, 12 h
O
O
Br
3
2
1
ArB(OH)2
4a−4i,
P(PPh3)4,
Na2CO3
DMF
room temperature,
6−7 h
Ar
4'
3'
1
7
O
6
2'
2
1'
5
3
O
4
5a−5i
the conjugated ketone functionality confirmed forma-
tion of benzofuran skeleton. Main peak in the mass
spectrum of compound 5a at m/z 313 corresponding to
[M + H]+ ion also confirmed the proposed Suzuki
coupled product.
The activity was determined using cup plate agar
diffusion method by measuring the zone of inhibition
in mm. The compounds were screened at concentration
50 μg/mL in DMSO. From the screening study it was
evident that compounds 5a, 5e, 5f, and 5g showed
good antibacterial activity against all the tested orga-
nisms (Table 2).
All the compounds were screened for their anti-
bacterial activity [24] against Staphylococcus aureus,
Bacillus subtilis, Pseudomonas aeruginosa and
Escherichia coli using Ampicillin as a reference drug.
In addition, all the compounds were screened for
their antifungal activity [25] against Aspergillus nigerzeae,
Penicillium italicum and Fusarium oxysporum using
Grieseofulvin as a reference drug. The activity was
determined using cup plate agar diffusion method by
measuring the zone of inhibition in mm. The
compounds were screened at concentration 50 μg/mL
in DMSO. The screening revealed that compounds 5a,
5e, and 5f showed good antifungal activity against all
the tested organisms (Table 3).
Table 1. Synthesis of compounds 5a–5i
Comp no.
Ar
Time, h Yield, %
5a
5b
5c
5d
5e
5f
Ph
6
6
7
6
7
7
6
7
6
76
72
74
70
68
75
73
65
74
4-FC6H4
4-ClC6H4
4-BrC6H4
In summary, substituted [1,1'-biphenyl]-4-yl(3-methyl-
benzofuran-2-yl)methanones were successfully syn-
thesized by Suzuki cross-coupling reaction. Title com-
pounds were prepared in good yields with Pd(PPh3) in
DMF in the presence of Na2CO3. Antibacterial and
antifungal activity studies revealed that some of them
showed good antibacterial and antifungal activity
against all the tested organisms.
2,4-Cl2C6H3
4-MeC6H4
4-MeOC6H4
4-CH3C(O)C6H4
1-Naphth
5g
5h
5i
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 12 2016

SYNTHESIS AND ANTIMICROBIAL EVALUATION
Table 2. Antibacterial activity of compounds 5a–5i
2793
Zone of inhibition, mm
Compound
gram positive bacteria
gram negative bacteria
Staphylococcus aureus
Bacillus subtilis Pseudomonas aeruginosa
Escherichia coli
5a
29
20
18
15
28
28
27
18
20
30
11
7
10
5
27
22
18
21
28
26
28
20
24
30
5b
5c
10
9
6
5d
8
5e
11
11
10
10
8
9
5f
8
5g
8
5h
5i
4
9
Ampicillin
12
10
1
EXPERIMENTAL
trum, ν, cm–1: 1077 (C–O–C), 1749 (C=O). H NMR
spectrum (400 MHz, DMSO-d6), δ, ppm: 2.68 s (3H,
CH3), 7.33–7.52 m (5H, Ar–H), 7.66–7.73 m (3H, Ar–H),
7.76 d (2H, H3', J = 8.53 Hz), 7.99 d (1H, H3', J =
8.78 Hz), 8.19 d (2H, H2', J = 8.53 Hz). 13C NMR
spectrum (101 MHz, DMSO-d6), δC, ppm: 10.0, 112.5,
121.4, 123.3, 123.4, 127.0, 127.3, 128.1, 128.2, 128.9,
130.4, 131.3, 131.6, 136.5, 140.0, 145.3, 148.4, 154.3,
185.4. Found, %: C 84.62; H 5.20; O 10.27. C22H16O2.
Calculated, %: C 84.59; H 5.16; O 10.24. M 313
[M + H]+.
Stuart SMP30 apparatus was used for determination
of melting points. Purity of the compounds was
checked by TLC on silica gel 60 F254 (Merck). H and
1
13C NMR spectra were recorded on a Bruker Avance II
400 spectrometer using TMS as an internal reference.
IR spectra were recorded in KBr on a Shimadzu FTIR
8400S spectrophotometer. Mass spectra were recorded
on a Shimadzu GCMS-QP 1000 mass spectrometer.
Elemental analysis was carried out on a Vario-11CHN
analyzer.
General procedure for the synthesis of [1,1'-
biphenyl]-4-yl(3-methylbenzofuran-2-yl)methanones
(5a–5i). Pd(PPh3)4 (0.10 mmol), arylboronic acid
(1.30 mmol) 4a–4i and Na2CO3 (3.00 mmol) were
added sequentially to a solution of 4-(bromophenyl)(3-
methylbenzofuran-2-yl)methanone 3 (1 mmol) in DMF
(5 mL). The round-bottom flask with the reaction
mixture was filled with nitrogen for 15 min. Then, the
reaction mixture was stirred at 80°C for 6–7 h under
nitrogen. The mixture was cooled to room temperature,
diluted with EtOAc (15 mL), and washed with H2O
and brine. The organic layer was dried over anhydrous
magnesium sulfate. The solvent was evaporated and
the residue was purified by the means of silica gel
column chromatography eluting with ethylacetate–
hexane (1 : 3) to afford pure product 5a–5i.
Table 3. Antifungal activity of compounds 5a–5i
Zone of inhibition, mm
Compound
Aspergillus
nigerzeae
Penicillium
italicum
Fusarium
oxysporum
5a
15
7
25
15
12
10
21
21
14
18
14
20
28
18
14
10
23
24
19
15
20
25
5b
5c
6
5d
8
5e
14
14
8
5f
5g
5h
5i
10
9
[1,1'-Biphenyl]-4-yl(3-methylbenzofuran-2-yl)-
methanone (5a). White solid, mp 152–154°C. IR spec-
Griseofulvin
12
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 12 2016

2794
B.J. REDDY, V.P. REDDY
(4'-Fluoro-[1,1'-biphenyl]-4-yl)(3-methylbenzo-
(4'-Methyl-[1,1'-biphenyl]-4-yl)(3-methylbenzo-
furan-2-yl)methanone (5f). White solid, mp 142–
144°C. IR spectrum, ν, cm–1: 1075 (C–O–C), 1747
furan-2-yl)methanone (5b). White solid, mp 150–
152°C. IR spectrum, ν, cm–1: 1077 (C–O–C), 1749
(C=O). 1H NMR (400 MHz, DMSO-d6), δ, ppm: 2.68 s
(3H, CH3), 7.17–7.34 m (4H, Ar–H), 7.51–7.58 m (3H,
Ar–H), 7.71–7.40 m (3H, Ar–H, H3'), 8.19 d (2H, H2',
1
(C=O). H NMR spectrum (400 MHz, DMSO-d6), δ,
ppm: 2.41 s (3H, CH3), 2.67 s (3H, CH3), 7.33–7.48 m
(5H, Ar–H), 7.64–7.71 m (3H, Ar–H), 7.76 d (2H, H3',
J = 8.53 Hz), 7.99 d (1H, H3', J = 8.78 Hz), 8.21 d (2H,
H2', J = 8.53 Hz). 13C NMR spectrum (101 MHz,
DMSO-d6), δC, ppm: 10.4, 22.4, 111.5, 122.2, 123.5,
124.8, 127.4, 127.4, 128.1, 128.9, 130.7, 131.6, 136.5,
140.0, 148.4, 154.3, 184.5. Found, %: C 84.67; H 5.58;
O 9.84. C23H18O2. Calculated, %: C 84.64; H 5.56; O
9.80. M 327 [M + H]+.
13
J = 8.53 Hz). C NMR spectrum (101 MHz, DMSO-
d6), δC, ppm: 10.0, 112.2, 116.2, 121.4, 123.3, 124.5,
124.6, 127.0, 128.2, 128.9, 129.0, 129.2, 129.7, 129.8,
129.9, 130.6, 130.7, 136.8, 140.1, 154.3, 185.4. Found,
%: C 80.03; H 4.60; O 9.72. C22H15FO2 Calculated, %:
C 79.99; H 4.58; O 9.69. M 331 [M + H]+.
(4'-Chloro-[1,1'-biphenyl]-4-yl)(3-methylbenzo-
furan-2-yl)methanone (5c). White solid, mp 161–
163°C. IR spectrum, ν, cm–1: 1078 (C–O–C), 1749
(4'-Methoxy-[1,1'-biphenyl]-4-yl)(3-methylbenzo-
furan-2-yl)methanone (5g). White solid, mp 168–
170°C. IR spectrum, ν, cm–1: 1079 (C–O–C), 1750
1
(C=O). H NMR spectrum (400 MHz, DMSO-d6), δ,
1
ppm: 2.68 s (3H, CH3), 7.15–7.34 m (4H, Ar–H), 7.49–
7.58 m (3H, Ar–H), 7.71–7.40 m (3H, Ar–H, H3'), 8.19
d (2H, H2', J = 8.53 Hz). 13C NMR spectrum
(101 MHz, DMSO-d6), δC, ppm: 10.0, 111.2, 116.4,
121.4, 123.7, 124.5, 124.6, 127.0, 128.2, 128.9, 129.0,
129.1, 129.7, 129.7, 129.9, 130.6, 130.7, 137.8, 140.1,
154.3, 185.4. Found, %: C 76.21; H 4.39; O 9.26.
C22H15ClO2. Calculated, %: C 76.19; H 4.36; O 9.23.
M 347 [M + H]+.
(C=O). H NMR spectrum (400 MHz, DMSO-d6), δ,
ppm: 2.71 s (3H, CH3), 3.94 s (3H, OCH3), 7.34–7.54
m (4H, Ar–H), 7.63–7.78 m (3H, Ar–H), 7.81 d (2H,
H3', J = 8.53 Hz), 7.87 d (1H, H3', J = 8.78 Hz), 8.09 d
13
(2H, H2', J = 8.53 Hz). C NMR spectrum (101 MHz,
DMSO-d6), δC, ppm: 10.4, 54.5, 112.5, 121.2, 123.3,
126.8, 127.4, 128.4, 128.1, 128.9, 130.1, 130.7, 131.6,
136.5, 140.0, 145.3, 148.4, 154.3, 184.5. Found, %: C
80.72; H 5.33; O 14.06 C23H18O3. Calculated, %: C
80.68; H 5.30; O 14.02. M 343 [M + H]+.
(4'-Bromo-[1,1'-biphenyl]-4-yl)(3-methylbenzo-
furan-2-yl)methanone (5d). White solid, mp 154–
156°C. IR spectrum, ν, cm–1: 1074 (C–O–C), 1749
1-(4'-(3-Methylbenzofuran-2-carbonyl)-[1,1'-bi-
phenyl]-4-yl)ethanone (5h). White solid, mp 165–
167°C. IR spectrum, ν, cm–1: 1072 (C–O–C), 1744
1
(C=O). H NMR spectrum (400 MHz, DMSO-d6), δ,
ppm: 2.67 s (3H, CH3), 7.18–7.37 m (4H, Ar–H), 7.47–
7.58 m (3H, Ar–H), 7.71–7.40 m (3H, Ar–H, H3'), 8.23
d (2H, H2', J = 8.53 Hz). 13C NMR spectrum (101
MHz, DMSO-d6), δC, ppm: 10.0, 111.2, 116.4, 121.4,
123.7, 124.5, 124.6, 127.0, 128.2, 128.9, 129.0, 129.1,
129.7, 129.7, 129.9, 130.6, 130.7, 137.8, 140.1, 154.3,
185.4. Found, %: C 67.56; H 3.90; O 8.20. C22H15BrO2.
Calculated, %: C 67.53; H 3.86; O 8.18. M 3911 [M + H]+.
1
(C=O). H NMR spectrum (400 MHz, DMSO-d6) δ,
ppm: 2.65 s (3H, CH3), 2.72 s (3H, CO–CH3), 7.20–
7.37 m (5H, Ar–H), 7.47–7.58 m (3H, Ar–H), 7.72 d
(2H, H3', J = 8.53 Hz), 8.20 d (2H, H2', J = 8.53 Hz).
13C NMR spectrum (101 MHz, DMSO-d6), δC, ppm:
10.0, 111.2, 115.4, 119.4, 123.7, 124.2, 124.6, 127.0,
128.2, 128.9, 129.0, 129.1, 129.7, 129.7, 129.9, 130.6,
130.7, 137.8, 140.1, 154.3, 185.4. Found, %: C 81.37;
H 5.16; O 13.59. C24H18O3. Calculated, %: C 81.34; H
5.12; O 13.54. M 355 [M + H]+.
(2',4'-Dichloro-[1,1'-biphenyl]-4-yl)(3-methylbenzo-
furan-2-yl)methanone (5e). White solid, mp 148–
150°C. IR spectrum, ν, cm–1: 1077 (C–O–C), 1749
1
(3-Methylbenzofuran-2-yl)[4-(naphth-1-yl)phenyl]-
(C=O). H NMR spectrum (400 MHz, DMSO-d6), δ,
methanone (5i). White solid, mp 140–142°C. IR spec-
ppm: 2.69 s (3H, CH3), 7.20–7.37 m (3H, Ar–H), 7.47–
7.58 m (3H, Ar–H), 7.71–7.38 m (3H, Ar–H, H3'), 8.20
d (2H, H2', J = 8.53 Hz). 13C NMR spectrum
(101 MHz, DMSO-d6), δC, ppm: 10.0, 111.2, 116.4,
121.4, 123.7, 124.5, 124.6, 127.0, 128.2, 128.9, 129.0,
129.1, 129.7, 129.7, 129.9, 130.6, 130.7, 137.8, 140.1,
154.3, 185.4. Found, %: C 69.33; H 3.75; O 8.43.
C22H14Cl2O2. Calculated, %: C 69.31; H 3.70; O 8.39.
M 381 [M + H]+.
1
trum, ν, cm–1: 1075 (C–O–C), 1748 (C=O). H NMR
spectrum (400 MHz, DMSO-d6), δ, ppm: 2.71 s (3H,
CH3), 7.34–7.75 m (10H, Ar–H), 7.90–7.95 m (3H,
13
Ar–H), 8.25 d (2H, H2', J = 8.53 Hz). C NMR spec-
trum (101 MHz, DMSO-d6), δC, ppm: 10.1, 112.3,
121.4, 123.3, 125.3, 125.7, 126.0, 126.3, 127.0, 128.2,
128.3, 128.4, 129.2, 129.8, 130.1, 131.2, 133.8, 136.6,
139.2, 145.3, 148.4, 154.3, 185.5. Found, %: C 86.19;
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 12 2016

SYNTHESIS AND ANTIMICROBIAL EVALUATION
2795
H 5.06; O 8.87. C28H18O2. Calculated, %: C 86.16; H
25±1°C for 5 days. Grieseofulvin used as fungicide
reference drug at concentration 50 µg/mL was also
tested under the same conditions against the discussed
fungi. Each treatment was done three times. The radial
growth of the fungal colonies was measured on the
sixth day. In vitro inhibition effect of the test
compounds towards the fungi was calculated in terms
of inhibition zone in mm (Table 3). The composition
of potato dextrose agar medium for fungi was: potatoes
(200 g), dextrose (20 g), agar (20 g), and distilled
water (1000 mL).
5.01; O 8.83. M 363 [M + H]+.
Biological assay. All synthesized compounds were
screened for their antibacterial activity against dif-
ferent types of bacterial strains, namely gram negative
bacterial strains of Pseudomonas aeruginosa and
Escherichia coli, and gram positive bacterial strains of
Bacillus subtilis and Staphylococcus aeureus.
The cultures were diluted with 5% saline and
autoclaved; the final volume was of approximate con-
centration 105–106 CFU/mL. Benzofuran derivatives
5a–5i were dissolved in dimethyl sulfoxide to achieve
concentration 50 μg/mL for antibacterial activity
measurement. For agar disc diffusion method, liquid
form of the test compound was soaked on the disc and
then allowed to dry in air, such that the disc got
completely saturated with the test compound. The
saturated discs were introduced onto the upper layer of
the medium evenly floated with the bacterial strain.
Composition of the nutrient agar medium for the
bacteria was agar (15 g), peptone (5 g), yeast extract
(3 g), NaCl (5 g), and distilled water (1000 mL).
ACKNOWLEDGMENTS
The authors are thankful to the head of the
chemistry department of Osmania University,
Hyderabad for providing laboratory facilities and B.
Jagadeesh is thankful to UGC, New Delhi, India for
financial support in the form of UGC-SRF. The
authors are also thankful to the director, CFRD,
Osmania University, Hyderabad for providing facilities
for the elemental and spectral analyses.
REFERENCES
The discs were dipped in different samples with the
investigated compounds, then were placed over the
evenly spread bacterial nutrient media and incubated at
37°C for 24 to 48 h to achieve the best results.
Afterwards zones of inhibition were measured. All the
experiments were carried out three times and the
results were expressed as zone of inhibition in mm
(Table 2). These zones of inhibition for the synthesized
compounds were compared with the zone of inhibition
for the referent antibiotic Amoxicillin used at con-
centration of 50 µg/mL which was also tested under
the same conditions against these bacterial species.
1. Nizami, S.A., Gurumurthy, M., Chattarjee, S., and
Panda, D., J. Adv. Pharm. Res., 2010, vol. 1, p. 26.
2. Fittig, R., and Ebert, G., Ann Chem., 1883, vol. 216,
p. 162.
3. Urzua, A., Rezende, M.C., Mascayano, C., and
Vásquez, L., Molecules, 2008, vol. 13, p. 882. doi
10.3390/molecules13040822
4. Aruna Kumar, D.B., Prakash, G.K., Kumarasamy, M.N.,
Nandheswarappa, B.P., Sheringara, B.S., and
Mahadevan, K.M., Indian J. Chem. B, 2007, vol. 46,
p. 336.
5. Gundogdu, K.N., Kadriya, B., Yagmur, T., Umit, U.,
and Seref, D., Eur. J. Med. Chem., 2006, vol. 41,
p. 6516. doi 10.1016/j.ejmech.2005.12.013
6. Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H.,
Naruto, S., and Sugano, Y., Bioorg. Med. Chem. Lett.,
2004, vol. 14, p. 455. doi 10.1016/j.bmcl.2003.10.039
Antifungal activity of the synthesized compounds
was tested against three pathogenic fungi, namely
Aspergillus nigerzeae, Penicillium italicum, and Fusarium
oxysporum by the poison plate technique.
The fungi were incubated in PDA at 25±1°C for
5 days to get new mycelium for antifungal assay; then
a mycelia as disks of approximately 0.45 cm diameter
cut from the culture medium were picked up with a
sterilized inoculation needle and inoculated in the
center of PDA plate. The test compounds were
dissolved in dimethyl sulfoxide, then added to the
ptato dextrose agar medium (PDA). Final concentra-
tion of the compounds in the medium was adjusted to
50 μg/mL. The inoculated plates were incubated at
7. Galal, S.A., All, A.E., Abdullah M.M., and Diwani, E.H.,
Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2420. doi
10.1016/j.bmcl.2009.03.069
8. Santana, L., Teijeira, M., Uriarte, E., Teran, C., Linares, B.,
Villar, R., Laguna, R., and Cano, E., Eur. J. Pharm.
Sci., 1999, vol. 7, p. 161. doi 10.1016/s0928-0987(98)
00019-0
9. Kirilmis, C., Ahmedzade, M., Suleyman, S., Koca, M.,
and Kizirgil, A., Eur. J. Med. Chem., 2008, vol. 43,
p. 300. doi 10.1016/j.ejmech.2007.03.023
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 12 2016

2796
B.J. REDDY, V.P. REDDY
10. Aslam, S.N., Stevenson, P.C., Phythian, S.J., Veitch, N.C.,
and Hall, D.R., Tetrahedron, 2006, vol. 62, p. 4214. doi
10.1016/j.tet.2006.02.015
11. Malik, W.U., Mahesh, V.K., and Raishighani, M.,
Indian J. Chem, 1971, vol. 9, p. 655.
12. Fry, D.J., Ficken, E.G., and Burrows. R.W., Brit., 1969,
18. Suzuki, A., Pure Appl. Chem., 1994, vol. 66, p. 213. doi
10.1351/pac199466020213
19. Suzuki, A., Pure Appl. Chem., 1991, vol. 63, p. 419. doi
10.1351/pac199163030419
20. Miyaura, N., and Suzuki, A., Chem. Rev., 1995, vol. 95,
p. 2457.
vol. 1, p. 168495.
21. Alonso, F., Beletskaya, I.P., and Yus, M., Tetrahedron,
13. Brady, B.A., Kennedy, J.A., and Sullivan, W.I.,
Tetrahedron, 1973, vol. 29, p. 359. doi 10.1016/s0040-
4020(01)93302-2
2008, vol. 64, p. 3047. doi 10.1016/j.tet.2007.12.036
22. Mondal, M., and Bora, U., Green Chem., 2012, vol. 14,
p. 1873. doi 10.1039/c2gc354016
14. Modern Arylation Methods, Ackermann, L., Ed., Wiley-
23. Yadav, N., Hussain, M.K., Ansari, M.I., Gupta P.K.,
and Hajela, K., RSC Advances, 2013, vol. 3, p. 540. doi
10.1039/C2RA22355D
VCH, Weinheim, 2009.
15. Suzuki, A., Boronic Acids. Preparation, Applications in
Organic Synthesis and Medicine, Weinheim: Wiely-
VHC, 2005, p. 123.
16. Bringmann, G., Mortimer, A.J.P., Keller, P.A., Gres-
ser, M.J., Garner, J., and Breuning, M., Angew. Chem.
Int. Ed., 2005, vol. 44, p. 5384. doi 10.1002/anie20046261
24. Ajjanna, M.S., Venugopala Reddy, K.R., Keshavayya, J.,
Ambika, V., Gopinath, V.S., Bosei, P., Goud, S.K., and
PeethambarI, S.K., J. Braz. Chem. Soc., 2011, vol. 22,
p. 849. doi 10.1590/s0103-50532011000500006
25. Song, S.Q., Zhou, L.G., Li, D., Tang, D., Li, J.Q., and
17. Miyaura, N., Yamada, K., and Suzuki, A., Tetrahedron
Lett., 1979, vol. 20, p. 3437.
Jiang, W.B., Nat. Prod. Res. Dev., 2004, vol. 16, p. 157.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 12 2016