Decarboxylative Arylation of Pyridine 1-Oxides and Anilides with Benzoic Acid via Palladium-Catalyzed C–H Functionalization

Article abstract of DOI:10.1002/ejoc.201801373

A novel method for the palladium-catalyzed decarboxylative ortho C–H bond arylation of pyridine 1-oxides and anilides with benzoic acids as aryl sources is described. The established methodology provides a direct approach for the synthesis of 2-arylpyridine 1-oxides and 2-aryl anilides in good isolated yields.

Full text of DOI:10.1002/ejoc.201801373

A Journal of
Accepted Article
Title: Decarboxylative Arylation of Pyridine 1-Oxides and Anilides with
Benzoic Acid via Palladium-Catalyzed C-H Functionalization
Authors: Minoo Dabiri, Seyed Iman Alavioon, and Siyavash Kazemi
Movahed
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201801373
Link to VoR: http://dx.doi.org/10.1002/ejoc.201801373
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10.1002/ejoc.201801373
European Journal of Organic Chemistry
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Decarboxylative Arylation of Pyridine 1-Oxides and Anilides with
Benzoic Acid via Palladium-Catalyzed C-H Functionalization
Minoo Dabiri*, Seyed Iman Alavioon and Siyavash Kazemi Movahed
Abstract:
A
novel method for the palladium-catalyzed
prevention of stroke, myocardial infarct and cardiovascular
decarboxylative ortho C-H bond arylation of pyridine 1-oxides and
inflammatory diseases (A),[17] P38 Kinase inhibitors (B[18] and
anilides with benzoic acids as aryl sources is described. The
C[19]), C-FMS kinase inhibitors (D)[20]
, treatment of kidney
disorders (E)[21], and anti-cancer (F)[22] (Figure 1).
established methodology provides
a
direct approach for the
synthesis of 2-arylpyridine 1-oxides and 2-ayl anilides in good
isolated yields.
Introduction
During the early decades, the inert C-H bonds activation to
prepare compounds with various properties was
a great
challenge for organic chemists.[1] But nowadays, there are many
reports in the literatures about transition metals-catalyzed C-H or
C-heteroatom activation to replace hydrogen or heteroatom with
different functional groups.[2] Transition metal catalyzed C-H
activation is
a
powerful tool for the selective C-H
functionalization using various active directing groups such as
imines, amides, carbonyls, heterocycles, etc.[3,4] Directing groups
mainly are used for trigger C-H bond cleavage and
regioselective functionalization.
Figure 1. Examples of bioactive 2-arylpyridin 1-oxide and 2-aryl anilide
derivatives
Transition metal catalyzed C-C bond formation reaction is
one of the most important procedure in organic synthesis for the
synthesis of complex molecules from simple precursors via the
one-step proceeding.[5] Carboxylic acids as aryl source for C-C
bond formation have unique advantages.[6] They are cheap, non-
toxic, stable, widely commercially available, and ease of
handling relative to expensive and/or sensitive organometallic
reagents.[7] Since the first report by Nilsson regarding the
copper-mediated decarboxylative biaryl coupling,[8] the exciting
Moreover, pyridine 1-oxides frequently are used as
protecting groups, auxiliary agents in asymmetric substances
synthesis and oxidants in heterocycle materials synthesis.[23,24]
N-O bond in pyridine 1-oxides and carbonyl in aniliids as
instrumental directing groups for the transition metal catalyzed
ortho-C-H functionalization has previously been widely studied
to obtain one regio- and chemo-selective product[25] (Scheme 1).
Fagnou reported a new approach for the synthesis of 2-aryl
pyridine by using the inexpensive, commercially available, and
bench-stable pyridine 1-oxides as replacements of unstable 2-
pyridyl organometallic.[26] Toward anilides, Shi reported an
efficient method for the generation of C(sp2) -C(sp2) bonds via
palladium catalyzed C-H activation of N-alkylacetanilides with
arylboronic acid.[27] Pd-catalyzed decarboxylative ortho-arylation
of anilides with aryl acylperoxides was developed by Wang.[28]
Very recently, we reported the arylation of pyridine 1-
oxides with phenyl hydrazines using palladium supported on
mesoporous silica/graphene nanohybrid as the powerful
heterogeneous catalyst.[29] Based on above introduction and
also as part of our ongoing studies on the C-H activation
reactions and organic synthesis,[29–35] herein, we report the
successful palladium-catalyzed decarboxylative C-H arylation of
pyridine 1-oxides and anilides with benzoic acids (Scheme 1).
breakthroughs
have
been
achieved
by
Myers,[9–11]
Gooßen,[12,13,13,14] and others in the development of transition-
metal-catalyzed decarboxylative cross-coupling reactions. Tan
reported the Pd-catalyzed decarboxylative coupling of thiazoles
and benzoxazole with various substituted benzoic acids.[15] Su
reported the direct arylation of a wide range of indoles with
benzoic acids using Pd(TFA)2/Ag2CO3/propionic acid catalyst
system through a decarboxylation/C-H bond activation.[16]
2-Arylpyridin 1-oxide and 2-aryl anilide derivatives are the
main building blocks of compounds with diverse medicinal
properties such as PDE4 inhibitors for the treatment and
[a]
Prof. M. Dabiri, S. I. Alavioon and Dr. S. K. Movahed
Faculty of Chemistry and Petroleum Sciences
Shahid Beheshti University
Tehran 1983969411 Islamic Republic of Iran
E-mail: m-dabiri@sbu.ac.ir
Homepage: http://facultymembers.sbu.ac.ir/dabiri
Supporting information for this article is given via a link at the end of
the document.
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10.1002/ejoc.201801373
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hydroperoxide (TBHP), and di-tert-butyl peroxide (DTBP) were
tested and they showed low efficiency and yields (Table 1,
entries 12–15). The yield was decreased to 36% when the
reaction was done in the absence of the co-oxidant (Table 1,
entry 16). These results indicated that the oxidant and co-
oxidants were necessary for the decarboxylative arylation.
Additionally, the various solvents such as chlorobenzene,
dimethyl sulfoxide (DMSO), 1,2-dichloroethane (DCE), 1,2-
dimethoxyethane (DME), and dichloromethane (DCM) were
tested which afforded moderate to poor yields of product (Table
1, entries 17-21). Also, no improvement in the product yield was
observed even when the reaction temperature was increased
from 110 °C to 120 °C; however, the yield decreased when the
reaction temperature was increased to 100 °C (Table 1, entries
22 and 23).
Table 1. Optimization of the reaction condition for the decarboxylative
ortho C-H bond arylation of pyridine 1-oxide (1a) with benzoic acid (1b) [a]
Catalyst
(mol%)
Yield
[%][b]
Entry
1
Additive
Solvent
Pd(OAc)2 (10)
PdCl2 (10)
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
AgOAc/K2S2O8/TFA
AgBr/K2S2O8/TFA
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
PhCl
69
2
61
PdCl2(COD)
(10)
3
42
4
Pd(dba)2 (10)
27
Cu(OAc)2.H2O
(10)
5
66
Scheme 1. Some examples of the Palladium-catalyzed arylation of pyridine 1-
oxides and anilides. TFA= trifluoroacetic acid, TfOH= Triflic acid, MS=
molecular sieve
Trace
Trace
Trace
54
6
CuBr2 (10)
7
CuCl2 (10)
8
-
Results and Discussion
9
Pd(OAc)2 (5)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Our initial investigation began with the C-H arylation of
pyridine1-oxide (1a) with benzoic acid (2a) as a model reaction
in different conditions. Different solvents, catalysts, oxidants, co-
oxidants, and temperatures were tested to optimize the reaction
conditions (Table 1). Various palladium and copper-based
catalysts were first screened (Table 1, entries 1-7). The results
showed that the Pd(OAc)2 is the best catalyze for the reaction
(Table 1, entry 1). In the absence of the catalyst, the reaction did
not proceed (Table 1, entry 8). In the next step, the different
loading of Pd(OAc)2 were tested and the results showed that the
10 mol% catalyst loading was most effective and gave the
higher yield than 5 mol% of Pd(OAc)2 (Table 1, entries 1 and 9).
The effect of oxidant was also investigated and no improvement
in yields were observed in the presence of Ag2OAc and AgBr
(Table 1, entries 10 and 11). Additionally, in the absence of the
oxidant, the reaction did not proceed (Table 1, entry 12). The
different types of co-oxidants such as (NH4)2S2O8, tert-butyl
10
11
12
13
14
15
16
17
18
19
62
Trace
Trace
58
K2S2O8/TFA
Ag2CO3/(NH4)2S2O8/TFA
Ag2CO3/TBHP/TFA
Ag2CO3/DTBP/TFA
Ag2CO3/TFA
Trace
Trace
36
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Trace
38
DCE
DCM
34
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Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
Ag2CO3/K2S2O8/TFA
20
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
DME
45
21
DMSO
MeCN
MeCN
Trace
43
22[c]
23[d]
69
[a] pyridine 1-oxides (0.5 mmol), benzoic acid (1 mmol), catalyst (mol%),
oxidant (20 mol%), co-oxidant (2 eq.), TFA (0.4 mL), Time = 24 h, temp. =
110 °C. [b] isolated yield. [c] Temp. = 100 °C. [d] Temp. = 120 °C
[a] pyridine 1-oxide (0.5 mmol), benzoic acid (0.7 mmol), Pd(OAc)2 (10 mol-
%), Ag2CO3 (20 mol%) K2S2O8 (2.0 equiv.), TFA (0.4 mL), MeCN (2.0 mL),
temp. = 110 °C, time = 24 h. [b] isolated yield.
After optimizing the reaction condition, the reaction scope
and substituent effect were examined in the Pd-catalyzed
decarboxylative ortho C-H bond arylation of various pyridine 1-
oxides with benzoic acids under optimal condition (Table 2). The
derivatives bearing electron-donating and electron-withdrawing
substituents on both aromatic rings in starting materials reacted
and gave moderate to good yields. The presence of electron-
donating substituents on benzoic acids such as p-OMe and p-
Me resulted in slightly higher yield than electron-withdrawing
substituents such as p-F, p-Br and p-CF3 (Table 2, 3b, 3c, 3d,
3e, and 3f). The hindered benzoic acids such as o-NO2 and o-Br
reacted well and gave the desired products in moderate yields
(Table 2, 3g and 3h). The substituted effect on pyridine 1-oxides
was evaluated in the decarboxylative ortho C-H bond arylation.
The electron-donating substituents such as m-Me and 3,5-diMe
and electron-withdrawing substituents such as m-CO2Et, m-Cl,
p-CN on pyridine 1-oxides gave the arylated products (Table 2,
3i, 3j, 3k, 3l, and 3m). The electron-donating substituents on
pyridine 1-oxides provided higher arylated products yield than
electron-withdrawing substituents which could be attributed to
the electrophilic acyloxylation C–H activation to form a C–Pd
bond.[30] Additionally, the meta- substituted (-Cl) benzoic acid
reacted and good yield of the product (3n) was obtained.
Following our investigation of Pd-catalyzed decarboxylative
ortho C-H bond arylation, the arylation of N-phenylpivalamide
derivatives with benzoic acids was evaluated. The C-H arylation
between N-phenylpivalamide (4a) and benzoic acid (2a) was
chosen as the model reaction. The reaction conditions was
optimized and the different conditions such as solvent, catalyst,
oxidant, co-oxidant, and temperature were tested (Table S1).
The various metal salts catalysts such as Pd(OAc)2, PdCl2,
PdCl2(COD) (COD
= 1,5-cyclooctadiene), Pd(dba)2 (dba =
dibenzylideneacetone), Cu(OAc)2.H2O, and CuCl2 were tested
and Pd(OAc)2 showed the best result (Table S1, entries 1-6). In
the absence of the catalyst, the reaction did not proceed (Table
S1, entry 7). The decrease of the Pd loading to 5 mol % afforded
a lower yield (47%) (Table S1, entry 8). The effect of oxidant
was also investigated and no improvement in yields was
observed in the presence of AgOAc and AgBr (Table S1, entries
9 and 10). The reaction did not proceed in the absence of the
oxidant (Table S1, entry 11). The different types of co-oxidants
were tested and they showed low efficiency and afforded low
yields (Table S1, entries 12 and 13). The reaction was carried
out in the absence of the co-oxidant and yield was decreased to
9% (Table S1, entry 14). Additionally, the various solvents were
tested which afforded moderate to poor yields of product (Table
S1, entries 15-17). Also, no improvement in the product yield
was observed even when the reaction temperature was
increased from 110 °C to 130 °C; however, the yield decreased
when the reaction temperature was increased to 90 °C (Table
S1, entries 18 and 19).
Table 2. Pd-catalyzed decarboxylative ortho C-H bond arylation of various
pyridine 1-oxides with benzoic acids
The substituted anilides and benzoic acids were reacted
under the optimized conditions to afford the corresponding
ortho-arylated anilides in good yields. The results are
summarized in Table 3. Anilides with both electron-donating and
electron-withdrawing substituents reacted good and resulted in
the corresponding 2-aryl anilides in moderate to good yields.
Anilides bearing electron-donating substituents such as p-Me
and p-OMe (Table 3, 5f and 5j) gave higher yields than electron-
withdrawing substituents p-Cl and p-CF3 (Table 3, 5i and 5h).
The electron-donating and electron-withdrawing substituents on
benzoic acids reacted slightly and gave ortho-arylated anilides in
moderate to good yields (Table 3, 5c, 5d, 5e, and 5f).
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Additionally, the meta- substituted (-Me) benzoic acid reacted
and good yield of the product (5o) was obtained. In addition to
the acetamido group, phenyl moieties were tested in this ortho-
C-H bond arylation and the product (5p) was isolated in good
yield.
Table 3. Pd-catalyzed decarboxylative ortho C-H bond arylation of various
anilides with benzoic acids
Scheme 2. The possible mechanism for Pd-catalyzed decarboxylative ortho
C-H bond arylation of pyridine 1-oxide
Conclusions
In conclusion, an efficient method for the ortho C–H bond
arylation of pyridine 1-oxides and anilides with benzoic acids as
aryl sources has been disclosed. The synthetic method allows
the synthesis of a broad range of 2-arylpyridine 1-oxides and 2-
aryl anilides with inexpensive and accessible starting materials.
A wide substrates tolerance with both electron-donating and
electron-withdrawing substituents on both coupling participants
is an advantage of the method. Moreover, the N-O bond in
pyridine 1-oxide and carbonyl in anilde as directing groups, in
the final product can easily remove to become pyridine and
aniline derivative.
Experimental Section
General Information. All solvents, pyridine aniline and benzoic acid
derivatives were purchased from Merck and Sigma. Other reagents were
purchased from commercial distributors and used without further
purification. Pyridine N-oxide and anilide derivatives were synthesized
according to the literatures.[39,40] Analytical thin layer chromatography
(TLC) was performed on pre-coated silica gel 60 F254 plates. The
products were purified by preparative column chromatography on silica
gel (0.063-0.200 mm; Merck). 1H and 13C-NMR Spectra: were recorded
on Bruker DRX 300 and INOVA 500 MHz advance instruments in CDCl3;
δ in ppm, J in Hz. Mass spectra were recorded on an Agilent Technology
(HP) 5973 Network Mass Selective Detector operating at an ionization
potential of 70 eV. IR spectra were recorded on a Bomem MB-Series FT-
IR spectrophotometer.
[a] anilide derivative (0.5 mmol), benzoic acid derivative (0.7 mmol), Pd(OAc)2
(10 mol-%), Ag2CO3 (20 mol%) K2S2O8 (2.0 equiv.), TFA (0.4 mL), MeCN (2.0
mL), temp. = 110 °C, time = 24 h. [b] isolated yield.
On the achieved results and based on the well-documented
literatures for the Pd-catalyzed the decarboxylative C-H bond
functionalization of various types of compounds via Pd0/PdII
mechanisms (Scheme 2).[16,36–38] In two intertwined catalytic
cycles, palladium acetate in the presence of TFA turns into
palladium trifluoroacetate (A). The palladium species performs
an electrophilic palladation (A to B) and the biaryl formation
through reductive elimination (C to 3a), whereas an AgI cation is
oxidized to an AgII cation by peroxodisulfate. Then, carboxylic
acid reacts with the AgII cation to form cation salt (E) by losing a
proton. The cation salt (E) further loses one molecule of CO2
and the AgI cation to form aryl radical (F). Finally, oxidation of
Pd0 to PdII (A), also performed by the K2S2O8, completes the
arylation cycle.
General Procedure for Synthesis of 2-phenylpyridine-1-oxides
Pyridine-1-oxides (0.5 mmol) and benzoic acid (0.7 mmol), MeCN (2 mL)
as solvent Ag2CO3 (20 mol%), K2S2O8 (2.0 equiv.), TFA (0.4 ml) and
Pd(OAc)2(10 mol % of Pd) were added to the tube and stirred at 110 oC
for 24 h. After this time, the mixture was cooled to room temperature,
diluted with CH2Cl2 and filtered. The residue was purified by column
chromatography to yield the optimal product.
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2-phenylpyridine 1-oxide (3a): Yellow solid, m.p.: 142–144 °C (lit.[41]
m.p.: 141-142 °C); IR (KBr, ꢀ/cm–1): 3076, 3013, 1490, 1397, 1229, 863,
760, 744, 671; 1H NMR (300 MHz, CDCl3) δ (ppm)= 8.40 (d, J = 6 Hz,
1H) , 7.84 – 7.81 (m, 2H), 7.62 (t, J = 6 Hz, 1H), 7.49-7.46 (m, 2H), 7.43-
7.38 (m, 3 H), 13C NMR (126 MHz, CDCl3): δ (ppm) = 139.43, 133.35,
129.65, 129.57, 128.22, 127.46, 126.53, 126.25, 124.52. MS (EI): m/z
(relative intensity %) = 172 (28) [M]+,170 (100), 154 (21), 142 (49), 127
(11), 117 (58), 51 (31).
126.25, 125.92, 123.42, 119.94. MS (IE) m/z (relative intensity %) 216 (5)
[M]+, 169 (10), 158 (10), 155 (15), 140 (17), 113 (21), 97 (34), 71 (63), 43
(100).
2-(2-bromophenyl)pyridine 1-oxide (3h): Yellow solid, m.p.: 110–
112 °C (lit.[43] m.p.: 113 °C); IR (KBr, ꢀ/cm–1): IR (KBr, ν/cm–1): 3049,
1637, 1432, 1325, 1243, 1109, 852, 745; 1H NMR (300 MHz, CDCl3) δ
(ppm)= 7.87 (d, J = 7.8 Hz, 1H), 7.69 – 7.62 (m, 2H), 7.50 (t, J = 7.6 Hz,
1H), 7.42 (d, J = 7.4 Hz, 1H), 7.35 -7.28 (m, 3H). 13C NMR (126 MHz,
CDCl3) δ (ppm)= 134.24, 133.68, 132.89, 132.30, 131.54, 131.02, 130.92,
128.10, 127.51, 127.10, 127.01. MS (IE) m/z (relative intensity %) 251
(48) [M+1]+, 250 (48) [M]+, 200 (37), 183 (49), 155 (21), 141 (41), 115
(58), 95 (23), 59 (100).
2-(4-methoxyphenyl)pyridine 1-oxide (3b): Yellow solid, m.p.: 125–
127 °C (lit.[41] m.p.: 121-123 °C); IR (KBr, ꢀ/cm–1): 3050, 2989, 1573,
1466, 1456, 1351, 1268, 1211, 1180, 829, 749; 1H NMR (300 MHz,
CDCl3) δ (ppm)= 8.37 (d, J = 5.5 Hz, 1H), 8.24 – 8.21 (m, 1H), 7.84 (d, J
= 8.6 Hz, 2H), 7.61 (d, J = 7.0 Hz, 1H), 7.37 (t, J = 2.8 Hz, 1H), 7.13 (d, J
= 8.6 Hz, 2H), 3.83 (s, 3H); 13C NMR (126 MHz, CDCl3): δ (ppm) =
160.57, 153.96, 142.53, 130.76, 126.88, 125.48, 123.81, 121.61, 113.71,
55.34. MS (EI): m/z (relative intensity %) = 201 (89) [M]+, 200 (100), 185
(31), 172 (26), 158 (40), 130 (51), 117 (21), 102 (10), 78 (24).
5-chloro-2-phenylpyridine 1-oxide (3i): Yellow solid, m.p.: 156–158 °C
IR (KBr, ꢀ/cm–1): 3036, 1612, 1509, 1489, 1321, 1275, 1214, 1098, 745,
673; 1H NMR (500 MHz, CDCl3) δ (ppm)= 7.62 (s, 1H), 7.29 – 7.24 (m,
2H), 6.97- 6.92 (m, 2H), 6.90 – 6.83 (m, 2H), 6.78 (d, J = 8.0 Hz, 1H), 13
C
NMR (126 MHz, CDCl3) δ (ppm)= 143.12, 137.14, 133.33, 129.35,
129.19, 128.34, 127.19, 122.98, 121.31. MS (EI): m/z (relative
intensity %) = 205 (18) [M]+, 203 (8), 150 (64), 108 (100), 92 (35), 77 (56),
65 (23).
2-(p-tolyl)pyridine 1-oxide (3c): Yellow solid, m.p.: 127–129 °C (lit.[41]
m.p.: 129-131 °C); IR (KBr, ꢀ/cm–1): 3046, 3081, 2929, 1630, 1427, 1251,
999, 827, 774; 1H NMR (500 MHz, CDCl3) δ (ppm)= 8.33 (d, J = 6.5 Hz,
1H), 7.73 (d, J = 7.8 Hz, 2H), 7.55 – 7.50 (m, 1H), 7.44 (d, J = 7.9 Hz,
2H), 7.28 – 7.22 (m, 2H), 2.38 (s, 3H); 13C NMR (126 MHz, CDCl3): δ
(ppm)= 140.38, 137.81, 133.05, 131.05, 129.06, 125.17, 123.26, 121.90,
22.21. MS (EI): m/z (relative intensity %) = 185 (71) [M]+, 184 (100), 156
(57), 149 (38), 117 (28), 95 (58), 69 (36), 57 (42).
5-(ethoxycarbonyl)-2-phenylpyridine 1-oxide (3j): Brown oil, IR (KBr,
ꢀ/cm–1): 3046, 1609, 1550, 1477, 1428, 1314, 1271, 1233, 1130, 1100,
965, 855, 804; 1H NMR (300 MHz, CDCl3): δ (ppm)= 8.37 (s, 1H), 8.11 (d,
J = 6.4 Hz, 1H), 7.43 (dd, J = 8.2, 1.7 Hz, 2H), 7.40 – 7.38 (m, 3H), 7.28
– 7.26 (m, 1H), 4.26 (q, J = 7.2 Hz, 2H), 1.31 (t, J = 7.1 Hz, 3H); 13C
NMR (126 MHz, CDCl3): δ (ppm)= 163.29, 138.96, 138.27, 136.82,
129.25, 128.58, 127.65, 124.16, 119.05, 116.81, 112.53, 39.14, 14.11.
MS (IE) m/z (relative intensity %) 244 (47) [M+1]+, 243 (47) [M]+, 171
(100), 155 (57), 79 (46), 57 (66).
2-(4-fluorophenyl)pyridine 1-oxide (3d): Yellow solid, m.p.: 163–
165 °C (lit.[41] m.p.: 161-163 °C); IR (KBr, ꢀ/cm–1): 3066, 3041, 2464,
1916, 1594, 1247, 1019, 759, 572; 1H NMR (300 MHz, CDCl3) δ (ppm)=
8.38 (d, J = 6.4 Hz, 1H), 7.90 – 7.85 (m, 2H), 7.46 – 7.42 (m, 1H), 7.34 –
7.28 (m, 1H), 7.19 (t, J = 8.5 Hz, 2H), 13C NMR (126 MHz, Chloroform-d)
δ (ppm): 163.32 (d, J = 250.2 Hz), 140.18, 136.14, 131.41 (d, J = 8.6 Hz),
128.60, 127.16, 125.66, 124.51, 116.39 (d, J = 21.7 Hz). MS (EI): m/z
(relative intensity %) = 189 (63) [M]+, 188 (100), 160 (31), 133 (35), 117
(28), 95 (15), 57 (42).
5-methyl-2-phenylpyridine 1-oxide (3k): Yellow solid, m.p.: 162–
164 °C (lit.[41] m.p.: 168-169 °C); IR (KBr, ꢀ/cm–1): 3058, 2965, 1609,
1532, 1478, 1377, 1325, 1254, 1103, 833, 737, 684; 1H NMR (300 MHz,
CDCl3): δ (ppm)= 8.24 (s, 1H), 7.96 (d, J = 6.4 Hz, 2H), 7.49 – 7.28 (m,
3H), 7.16 (d, J = 8.3 Hz, 2H), 2.54 (s, 3H); 13C NMR (126 MHz, CDCl3): δ
(ppm)= 145.90, 142.09, 138.72, 134.20, 130.26, 129.07, 127.82, 127.12,
124.82, 22.72. MS (EI): m/z (relative intensity %) = 185 (21) [M]+, 184
(32), 167 (16), 149 (72), 106 (68), 97 (49), 85 (57), 71 (73), 57 (100).
2-(4-bromophenyl)pyridine 1-oxide (3e): Brown oil. IR (KBr, ꢀ/cm–1):
3051, 1623, 1439, 1336, 1250, 1104, 840, 747; 1H NMR (300 MHz,
CDCl3) δ (ppm)= 8.01 (d, J = 8.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.48 –
7.44 (m, 3H), 7.37 (d, J = 8.2 Hz, 1H), 7.10 (t, J = 7.8 Hz, 1H). 13C NMR
(126 MHz, CDCl3) δ (ppm)= 143.15, 139.17, 136.66, 130.66, 129.63,
127.41, 122.62, 118.90, 115.77. MS (IE) m/z (relative intensity %) 251
(50) [M+1]+, 250 (50) [M]+, 200 (39), 183 (54), 155 (17), 141 (33), 115
(52), 95 (30), 59 (100).
2-(4-bromophenyl)-3,5-dimethylpyridine 1-oxide (3l): Brown oil, IR
(KBr, ꢀ/cm–1): 3055, 2965, 1619, 1556, 1460, 1388, 1331, 1254, 1116,
827, 740, 682; 1H NMR (500 MHz, CDCl3) δ (ppm)= 8.42 (s, 1H), 8.24 (s,
1H), 7.38 – 7.28 (m, 5H), 7.06 (s, 1H), 2.52 (s, 3H), 2.39 (s, 3H); 13C
NMR (126 MHz, CDCl3) δ (ppm)=136.12, 131.13, 131.07, 128.73, 127.11,
126.93, 126.19, 123.55, 23.75, 20.63. MS (IE) m/z (relative intensity %)
279 (49) [M+1]+, 278 (49) [M]+, 264 (70), 262, (58), 250 (34), 199 (61),
123 (42), 79 ( 64), 58 (100).
2-(4-(trifluoromethyl)phenyl)pyridine (3f): Yellow solid, m.p.: 125–
127 °C (lit.[26] m.p.: 127-129 °C); IR (KBr, ꢀ/cm–1): 2949, 1703, 1593,
1517, 1353, 1265, 1238, 1127, 745; 1H NMR (300 MHz, CDCl3) δ (ppm)=
8.48 – 8.45 (m, 2H), 8.06 – 8.02 (m, 2H), 7.73 (d, J = 8.2 Hz, 1H), 7.69 (d,
J = 8.2 Hz, 1H), 7.52 – 7.47 (m, 2H). 13C NMR (126 MHz, CDCl3) δ
(ppm)= 150.75, 144.06, 138.51, 135.01 (q, J = 32 Hz), 129.74, 127.94,
125.91, 125.10, 124.93, 123.9 (q, J = 272 Hz), 119.78. MS (IE) m/z
(relative intensity %) 239 (7) [M]+, 211 (7), 183 (12), 140 (100), 125 (11),
111 (21), 97 (38), 85 (43), 71 (48), 57 (62).
4-cyano-2-phenylpyridine 1-oxide (3m): Brown oil, IR (KBr, ꢀ/cm–1):
3050, 3017, 2994, 2226, 1555, 1475, 1452, 1368, 1259, 1247, 984, 857,
786; 1H NMR (300 MHz, CDCl3): δ (ppm)= 8.42 - 8.23 (m, 3H), 7.52 –
7.27 (m, 3H), 7.10 (d, J = 8.1 Hz, 2H); 13C NMR (126 MHz, CDCl3) δ
(ppm)= 151.78, 146.93, 142.38, 133.62, 131.89, 128.36, 125.14, 122.78,
121.08, 114.63. MS (EI): m/z (relative intensity %) = 196 (8) [M]+, 180
(26), 167 (42), 152(36), 105 (52), 93 (31), 77 (100), 51 (35).
2-(2-nitrophenyl)pyridine 1-oxide (3g): Yellow solid, m.p.: 157–159 °C
(lit.[42] m.p.: 160-161 °C); IR (KBr, ꢀ/cm–1): 3070, 3051, 1587, 1434, 1369,
1238, 1102, 926, 751; 1H NMR (300 MHz, CDCl3) δ (ppm)= 8.44 (d, J =
6.4 Hz, 1H), 8.24 – 8.22 (m, 3H), 8.02 (d, J = 8.5 Hz, 1H), 7.79 – 7.77 (m,
1H), 7.63 – 7.55 (m, 1H), 7.51 – 7.46 (m, 1H); 13C NMR (126 MHz,
CDCl3) δ (ppm)= 139.39, 135.53, 133.73, 132.42, 131.33, 130.06, 126.91,
2-(3-chlorophenyl)pyridine 1-oxide (3n): White solid, m.p. 81–83 °C;
IR (KBr, ꢀ/cm–1): 3046, 1613, 1511, 1483, 1325, 1266, 1220, 1086, 746,
1
667; H NMR (300 MHz, CDCl3): δ (ppm)= 8.48 (d, J = 8.3 Hz, 1H), 8.08
(d, J = 7.9 Hz, 1H), 7.84 - 7.79 (m, 4H), 7.56 – 7.52 (m, 2H); 13C NMR
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201801373
European Journal of Organic Chemistry
FULL PAPER
(126 MHz, CDCl3): δ (ppm)= 137.7, 133.0, 131.9, 130.9, 129.8, 128.9,
128.6, 124.4, 120.0. MS (EI): m/z (relative intensity %) = 205 (15), 149
(91), 121 (20), 93 (100), 77 (31), 57 (91), 41 (40).
N-(4',5-dimethyl-[1,1'-biphenyl]-2-yl)pivalamide (5f): White crystal,
m.p.: 102-104 °C (lit.[44] m.p.: 101-103 °C); IR (KBr, ꢀ/cm–1) 3248, 3027,
1652, 1524, 1291, 857, 701; 1H NMR (300 MHz, CDCl3), δ (ppm)= 8.24
(d, J = 8.1 Hz, 1H), 7.45 (br, 1H), 7.29 – 7.24 (m, 4H), 7.18 (d, J = 8.4 Hz,
1H), 7.06 (s, 1H), 2.44 (s, 3H), 2.36 (s, 3H), 1.13 (s, 9H), 13C NMR (126
MHz, CDCl3) δ (ppm)= 176.09, 137.65, 135.28, 133.36, 132.68, 132.17,
130.37, 129.60, 129.14, 128.72, 120.98, 39.69, 27.43, 21.19, 20.80. MS
(IE) m/z (relative intensity %) 281 (26) [M]+, 233 (60), 197 (32), 119 (14),
105 (100), 57 (41).
General Procedure for Synthesis of 2-aryl anilides
Anilide derivatives (0.5 mmol) and benzoic acid (0.7 mmol), MeCN (2
mL) as solvent, Ag2CO3 (20 mol%) K2S2O8 (2.0 equiv.), TFA (0.4 ml) and
Pd(OAc)2(10 mol % of Pd) were added to the tube and stirred at 110 oC
for 24 h. After this time, the mixture was cooled to room temperature,
diluted with CH2Cl2 and filtered. The residue was purified by column
chromatography to yield the desired product.
N-(5-bromo-4'-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5g): Yellow
crystal, m.p.: 99-101 °C (lit.[44] m.p.: 98-100 °C); IR (KBr, ꢀ/cm–1) 3274,
2952, 1630, 1564, 1206, 939, 754, 676; 1H NMR (300 MHz, CDCl3), δ
(ppm)= 8.31 (d, J = 8.8 Hz, 1H), 7.51 – 7.42 (m, 2H), 7.37 (br, 1H), 7.32
(d, J = 7.8 Hz, 2H), 7.24 (d, J = 7.8 Hz, 2H), 2.44 (s, 3H), 1.11 (s, 9H),
13C NMR (126 MHz, CDCl3) δ (ppm)= 176.31, 138.49, 134.44, 133.88,
133.63, 132.43, 131.05, 129.91, 129.01, 122.22, 116.39, 39.87, 27.37,
21.29. MS (IE) m/z (relative intensity %) 347 (61) [M+2]+, 345 (63) [M]+,
263 (34), 261 (47),180 (36),167 (27),149 (35), 57 (100), 41 (19).
N-([1,1'-biphenyl]-2-yl)pivalamide (5a): White crystal, m.p.: 68-70 °C
(lit.[28] m.p.: 65-67 °C); IR (KBr, ꢀ/cm–1) 3266, 1639, 1571, 940, 647; 1H
NMR (300 MHz, CDCl3), δ (ppm)= 8.38 (d, J = 8.3 Hz, 1H), 7.53 – 7.48
(m, 4H), 7.45 (d, J = 7.0 Hz, 1H), 7.38 (d, J = 7.6 Hz, 2H), 7.25 (br, 1H),
7.17 (t, J = 7.4 Hz, 1H), 1.11 (s, 9H), 13C NMR (126 MHz, CDCl3) δ
(ppm)= 176.32, 138.06, 135.13, 132.20, 129.74, 129.35, 129.07, 128.49,
128.09, 123.93, 120.91, 39.81, 27.39. MS (EI): m/z (relative intensity %)
= 253 (52) [M]+, 169 (61), 57(100), 41 (16 ).
N-(5-chloro-4'-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5h): Colorless
crystal, m.p.: 100-102 °C (lit.[44] m.p.: 102-104 °C); IR (KBr, ꢀ/cm–1) 3261,
1
2988, 1633, 1518, 1201, 826, 749; H NMR (400 MHz, CDCl3), δ (ppm)=
N-(5-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5b): Colorless crystal,
m.p.: 97-99 °C (lit.[44] m.p.: 94-96 °C); IR (KBr, ꢀ/cm–1) 3285, 2960, 1653,
8.36 (d, J = 8.8 Hz, 1H), 7.53 (br, 1H), 7.35 – 7.30 (m, 3H), 7.26 (s, 1H),
7.24 – 7.22 (m, 2H), 2.45 (s, 3H), 1.13 (s, 9H), 13C NMR (100 MHz,
CDCl3) δ (ppm)= 176.55, 143.60, 137.62, 135.15, 135.12, 128.78, 128.66,
128.48, 128.28, 123.85, 120.28, 39.88, 27.82, 21.18. MS (IE) m/z
(relative intensity %) 303 (41) [M+2]+, 301 (100) [M]+, 217 (84), 180 (26),
57 (71).
1
1558, 1268, 798, 688; H NMR (300 MHz, CDCl3), δ (ppm)= 8.29 (d, J =
8.7 Hz, 2H), 7.87 (d, J = 8.2 Hz, 1H), 7.54 (d, J = 8.6 Hz, 2H), 7.31 – 7.20
(m, 3H), 7.08 (d, J = 2.1 Hz, 1H), 2.37 (s, 3H), 1.12 (s, 9H), 13C NMR
(126 MHz, CDCl3) δ (ppm)= 176.29, 137.86, 135.24, 135.06, 132.08,
129.86, 129.74, 129.22, 128.29, 123.85, 120.78, 39.73, 27.45, 21.38. MS
(EI): m/z (relative intensity %) = 267 (67) [M]+, 210 (16), 183 (78), 182
(36), 167 (12), 57 (100), 41 (29).
N-(4'-methyl-5-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)pivalamide (5i):
Colorless crystal, m.p.: 87-89 °C (lit.[44] m.p.: 83-85 °C); IR (KBr, ꢀ/cm–1
)
3278, 2973, 1653, 1525, 1317, 883, 784; 1H NMR (400 MHz, CDCl3), δ
(ppm)= 8.61 (d, J = 8.7 Hz, 1H), 7.71 (br, 1H), 7.65 – 7.62 (m, 1H), 7.51
(d, J = 2.2 Hz, 1H), 7.43 – 7.33 (m, 2H), 7.32 – 7.17 (m, 2H), 2.48 (s, 3H),
1.14 (s, 9H), 13C NMR (126 MHz, CDCl3) δ (ppm)= 176.60, 138.75,
138.43, 133.60, 131.85, 130,08, 126.77 (q, J = 5.0 Hz),125.40 (q, J =
84.4 Hz), 125.40 (q, J = 5.0 Hz), 123.40 (q, J = 269.5 Hz), 120.10, 40.02,
27.34, 21.29. MS (IE) m/z (relative intensity %) 335 (67) [M]+, 278 (14),
251 (81), 250 (33), 248 (29), 235 (19), 18 (17), 85 (19), 57 (100), 41 (29).
N-(4'-bromo-5-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5c): Colorless
crystal, m.p.: 121-123 °C (lit.[44] m.p.: 122-124 °C); IR (KBr, ꢀ/cm–1) 3268,
2967, 1647, 1525, 1192, 912, 726, 663; 1H NMR (400 MHz, CDCl3), δ
(ppm)= 8.10 (d, J = 8.3 Hz, 1H), 7.62 (d, J = 8.4 Hz, 2H), 7.33 (br, 1H),
7.25 (d, J = 8.4 Hz, 2H), 7.21 – 7.16 (m, 1H), 7.04 (d, J = 2.5 Hz, 1H),
2.36 (s, 3H), 1.15 (s, 9H), 13C NMR (126 MHz, CDCl3) δ (ppm)= 176.31,
137.37, 134.09, 132.28, 132.03, 131.71, 130.99, 130.30, 129.32, 122.24,
122.09, 39.67, 27.49, 20.89. MS (EI): m/z (relative intensity %) = 347 (61)
[M+2]+, 345 (62) [M]+, 263 (37), 261 (44),180 (34),167 (27),149 (331), 57
(100), 41 (23).
N-(5-methoxy-4'-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5j): Colorless
crystal, m.p.: 105-107 °C (lit.[44] m.p.: 109-111 °C); IR (KBr, ꢀ/cm–1) 3286,
1
2997, 1662, 1547, 1271, 766, 699; H NMR (300 MHz, CDCl3), δ (ppm)=
N-(4'-chloro-5-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5d): Colorless
crystal, m.p.: 108-109 °C (lit.[44] m.p.: 105-107 °C); IR (KBr, ꢀ/cm–1) 3278,
2969, 1649, 1505, 1225, 821, 763; 1H NMR (400 MHz, CDCl3), δ (ppm)=
8.11 (d, J = 8.4 Hz, 1H), 7.48 – 7.44 (m, 2H), 7.33 – 7.31 (m, 3H), 7.21 –
7.18 (m, 1H), 7.05 (d, J = 2.1 Hz, 1H), 2.37 (s, 3H), 1.15 (s, 9H), 13C
NMR (126 MHz, CDCl3) δ (ppm)= 176.31, 136.90, 134.06, 132.36,
131.73, 130.68, 130.36, 129.36, 129.28, 129.08, 122.21, 39.67, 27.47,
20.86. MS (EI): m/z (relative intensity %) = 303 (10) [M+2]+, 301 (8) [M]+,
225 (29), 190 (85), 141 (65), 106 (30), 77 (22), 57 (100), 41 (24).
8.17 (d, J = 2.7 Hz, 1H), 7.61 (br, 1H), 7.32 – 7.22 (m, 4H), 7.13 (d, J =
8.4 Hz, 1H), 6.74 - 6.70 (m, 1H), 3.88 (s, 3H), 2.43 (s, 3H), 1.13 (s, 9H),
13C NMR (126 MHz, CDCl3) δ (ppm)= 176.40, 159.58, 137.54, 136.26,
134.87, 130.46, 129.77, 129.44, 214.17, 110.56, 105.08, 55.42, 39.95,
27.43, 21.23. MS (IE) m/z (relative intensity %) 297 (100) [M]+, 240 (15),
213 (562), 198 (59), 168 (16), 57 (33).
N-(4-chloro-4'-methyl-[1,1'-biphenyl]-2-yl)pivalamide
(5k):
White
crystal, m.p.: 80-82 °C lit.[45] m.p.: 78-81 °C); IR (KBr, ꢀ/cm–1) 3281, 2952,
1661, 1519, 1218, 856, 767; 1H NMR (300 MHz, CDCl3), δ (ppm)= 8.31
(d, J = 1.9 Hz, 1H), 7.55 (br, 1H), 7.32 – 7.25 (m, 4H), 7.17 (d, J = 7.7
Hz, 1H), 7.03 – 7.00 (m, 1H), 2.44 (s, 3H), 1.14 (s, 9H), 13C NMR (126
MHz, CDCl3) δ (ppm)= 176.25, 144.65, 137.60, 135.15, 135.12, 129.70,
129.66, 129.46, 129.28, 123.35, 120.20.39.81, 27.42, 21.19. MS (IE) m/z
(relative intensity %) 303 (45) [M+2]+, 301 (100) [M]+, 213 (53), 180 (18),
57 (37).
N-(5-methyl-4'-nitro-[1,1'-biphenyl]-2-yl)pivalamide
(5e):
Yellow
precipitate, m.p.: 132-134 °C (lit.[44] m.p.: 133-135 °C); IR (KBr, ꢀ/cm–1
)
3267, 3001, 1559, 1546, 1375, 786. 1H NMR (400 MHz, CDCl3), δ
(ppm)= 8.34 (d, J = 8.7 Hz, 2H), 7.96 (d, J = 8.3 Hz, 1H), 7.58 (d, J = 8.8
Hz, 2H), 7.30 – 7.25 (m, 1H), 7.19 (br, 1H), 7.10 (d, J = 2.3 Hz, 1H), 2.40
(s, 3H), 1.15 (s, 9H), 13C NMR (126 MHz, CDCl3) δ (ppm)= 176.50,
147.29, 145.69, 135.04, 131.96, 131.84, 130.28, 130.24, 130.20, 123.95,
123.72, 39.60, 27.46, 20.89. MS (EI): m/z (relative intensity %) = 312
(100) [M]+, 262 (28), 228 (73), 211 (36), 180 (43), 57 (81).
N-(4,4'-dimethyl-[1,1'-biphenyl]-2-yl)pivalamide (5l): Yellow oil, IR
(KBr, ꢀ/cm–1) 3275, 2942, 1676, 1570, 1248 , 764, 668; 1H NMR (300
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201801373
European Journal of Organic Chemistry
FULL PAPER
[3] Z. Chen, B. Wang, J. Zhang, W. Yu, Z. Liu, Y. Zhang, Org. Chem. Front. 2015,
2, 1107–1295.
MHz, CDCl3), δ (ppm)= 8.24 (s, 1H), 7.72 (br, 1H), 7.32 – 7.21 (m, 4H),
7.13 (d, J = 7.7 Hz, 1H), 6.97 (d, J = 7.8 Hz, 1H), 2.43 (s, 3H), 2.41 (s,
3H), 1.13 (s, 9H), 13C NMR (126 MHz, CDCl3) δ (ppm)= 176.35, 138.27,
137.65, 135.08, 134.98, 129.72, 129.68, 129.31, 124.66, 121.32, 39.84,
27.45, 21.53, 21.28. MS (IE) m/z (relative intensity %) 281 (52) [M]+, 224
(16), 197 (43), 180 (19), 167 (13), 149 (25), 57 (100), 41 (54).
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T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147–1169.
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N-(5-fluoro-4'-methyl-[1,1'-biphenyl]-2-yl)pivalamide (5m): Colorless
crystal, m.p.: 76-78 °C (lit.[44] m.p.: 75-77 °C); IR (KBr, ꢀ/cm–1) 3285,
2944, 1643, 1590, 1345, 1237, 759, 720, 649; 1H NMR (400 MHz, CDCl3),
δ (ppm)= 8.32 – 8.29 (m, 1H), 7.44 (br, 1H), 7.35 – 7.30 (m, 2H), 7.28 –
7.26 (m, 2H), 7.10 – 7.05 (m, 1H), 6.99 – 6.96 (m, 1H), 2.46 (s, 3H), 1.14
(s, 9H), 13C NMR (126 MHz, CDCl3) δ (ppm)= 176.29, 158.93 (d, J =
304.9 Hz), 138.37 (d, J = 8.8 Hz), 134.25 , 134.08, 131.27 (d, J = 3.8 Hz),
129.82, 128.97, 122.87 (d, J = 10.1 Hz), 116.45 (d, J = 27.7 Hz), 114.61
(d, J = 27.7 Hz), 39.71, 27.41, 21.27. MS (IE) m/z (relative intensity %)
285 (24) [M]+, 201 (27), 167 (33), 149 (68), 71 (26), 57 (100), 43 (31), 41
(56).
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[16] J. Zhou, P. Hu, M. Zhang, S. Huang, M. Wang, W. Su, Chem. – Eur. J. 2010,
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52, 5531–5545.
N-(4,5-dimethoxy-4'-methyl-[1,1'-biphenyl]-2-yl)pivalamide
(5n):
Brown oil, IR (KBr, ꢀ/cm–1) 3426, 2978, 1677, 1603, 1563, 1414, 1272,
765, 635; 1H NMR (400 MHz, CDCl3), δ (ppm)= 8.12 (s, 1H), 7.48 (br,
1H), 7.33 – 7.26 (m, 4H), 6.77 (s, 1H), 3.97 (s, 3H), 3.88 (s, 3H), 2.45 (s,
3H), 1.15 (s, 9H), 13C NMR (126 MHz, CDCl3) δ (ppm)= 176.27, 148.34,
145.15, 137.67, 129.74, 129.37, 128.72, 124.01, 112.81, 105.06, 56.16,
56.04, 39.78, 27.46, 21.24. MS (IE) m/z (relative intensity %) 327 (100)
[M]+, 228 (31), 211 (23), 196 (17), 57 (51).
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[24] A. Albini, Synthesis 1993, 1993, 263–277.
N-(3'-methyl-[1,1'-biphenyl]-2-yl)pivalamide(5o): White crystal, m.p.
85–87 °C (lit.[46] m.p.: 85-87 °C); IR (KBr, ꢀ/cm–1) 3268, 2978, 1671, 1580,
1
[25] B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 2008, 949–957.
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18020–18021.
1247 , 776, 656; H NMR (300 MHz, CDCl3): δ (ppm)= δ 8.36 (d, J = 8.2
Hz, 1H), 7.73 (d, J = 7.7 Hz, 1H), 7.57 (s, 1H), 7.47 (s, 1H), 7.42 - 7.34
(m, 2H), 7.24 – 7.17 (m, 3H), 2.43 (s, 3H), 1.13 (s, 9H).; 13C NMR (126
MHz, CDCl3): δ (ppm)= δ 176.5, 138.7, 137.9, 130, 129.7, 129.1, 129.0,
128.7, 128.3, 126.3, 125.2, 124.0, 39.8, 31.9, 27.3. MS (EI): m/z (relative
intensity %) = 267 (49), 210 (14), 183 (43), 152 (21), 115 (11), 85 (13),
57 (100).
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Acknowledgements
We gratefully acknowledge financial support from the Research
Council of Shahid Beheshti University.
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Keywords: Palladium • C-H functionalization • Arylation •
Synthetic methods • Carboxylic acids
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This article is protected by copyright. All rights reserved.

10.1002/ejoc.201801373
European Journal of Organic Chemistry
FULL PAPER
Layout 1:
FULL PAPER
A
novel method for
Decarboxylative arylation
palladium-catalyzed
Seyed Iman Alavioon, Siyavash
Kazemi Movahed and Minoo Dabiri*
decarboxylative ortho C-H
bond arylation of pyridine
1-oxides and anilides with
benzoic acids as aryl
sources are described.
Page No. – Page No.
Decarboxylative Arylation of
Pyridine 1-Oxides and Anilides
with Benzoic Acid via Palladium-
Catalyzed C-H Functionalization
This article is protected by copyright. All rights reserved.