Silver-catalyzed double-decarboxylative cross-coupling of α-keto acids with cinnamic acids in water: A strategy for the preparation of chalcones

Article abstract of DOI:10.1021/jo502642n

A silver-catalyzed double-decarboxylative protocol has been proposed for the construction of chalcone derivatives via cascade coupling of substituted α-keto acids with cinnamic acids under the mild aqueous conditions. The developed method for constructing C-C bonds via double-decarboxylative reactions is efficient, practical, and environmentally benign by using the readily available starting materials. It should provide a promising synthesis candidate for the formation of diverse and useful chalcone derivatives in the fields of synthetic and pharmaceutical chemistry.

Full text of DOI:10.1021/jo502642n

Subscriber access provided by LSU Libraries
Note
Silver-Catalyzed Double-Decarboxylative Cross-
Coupling of Alpha-Keto Acids with Cinnamic Acids
in Water: A Strategy for the Preparation of Chalcones
Ning Zhang, Daoshan Yang, Wei Wei, Li Yuan, Fafa Nie, Laijin Tian, and Hua Wang
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/jo502642n • Publication Date (Web): 20 Feb 2015
Downloaded from http://pubs.acs.org on February 22, 2015
Just Accepted
“Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted
online prior to technical editing, formatting for publication and author proofing. The American Chemical
Society provides “Just Accepted” as a free service to the research community to expedite the
dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts
appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been
fully peer reviewed, but should not be considered the official version of record. They are accessible to all
readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered
to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published
in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just
Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor
changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers
and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors
or consequences arising from the use of information contained in these “Just Accepted” manuscripts.
The Journal of Organic Chemistry is published by the American Chemical Society.
1155 Sixteenth Street N.W., Washington, DC 20036
Published by American Chemical Society. Copyright © American Chemical Society.
However, no copyright claim is made to original U.S. Government works, or works
produced by employees of any Commonwealth realm Crown government in the
course of their duties.

Page 1 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
Silver-Catalyzed Double-Decarboxylative Cross-Coupling of
Alpha-Keto Acids with Cinnamic Acids in Water: A Strategy for
8
9
the Preparation of Chalcones
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Ning Zhang, Daoshan Yang,* Wei Wei, Li Yuan, Fafa Nie, Laijin Tian, Hua Wang*
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical
Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical
Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. China.
*E-mail: yangdaoshan@tsinghua.org.cn; huawang_qfnu@126.com
ABSTRACT:
A silver-catalyzed double-decarboxylative protocol has been proposed for the
construction of chalcone derivatives via cascade coupling of substituted α-keto acids
with cinnamic acids under the mild aqueous conditions. The developed method for
constructing C-C bond via double decarboxylative reactions is efficient, practical and
environmentally-benign by using the readily available starting materials. It should
provide a promising synthesis candidate for the formation of diverse and useful
chalcone derivatives in the fields of synthetic and pharmaceutical chemistry.
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 2 of 22
1
2
3
4
5
6
7
8
9
Seeking mild, green and selective approaches for the formation of C-C bonds has
been of growing interest in organic chemistry.1 Historically, the C-C bond forming
reactions were mainly conducted by nucleophilic additions, substitutions, Diels-Alder
reactions and Friedel-Crafts-type reactions.2 Recently, the transition-metal catalyzed
or mediated coupling reactions have been emerging as the powerful tools for the C-C
bond formation. In this respect, pre-functionalized substrates such as organometallic
reagents, organohalides or pseudo halides are coupled in these transformations under
an aerobic conditions.3 As an alternative, decarboxylative reactions have been
introduced by Goossen,4 Myers,5 and other research groups.6 Recently, tremendous
progress has been made in the decarboxylative-coupling transformations using
carboxylic acids as the substrates owing to such coupling partners are easy to store
and handle.7 Notably, cinnamic acids and α-keto acids have been standing out as the
remarkable coupling partners in decarboxylative transformations. In recent years,
using α-keto acids as substrates in the decarboxylative reactions has been extensively
studied, such as the visible-light-mediated amidations,8 difunctionalization of
activated alkenes,9 and decarboxylative acylation of aromatic C-H bonds.10 On the
other hand, decarboxylation of cinnamic acids have also been investigated, such as the
transition-metal catalyzed decarboxylative coupling of aryl or vinyl halides with
cinnamic acids,11 radical pathways to formation C-C bond,12 C-N bond13 and C-S
bond.14 Meanwhile, α-keto acids and cinnamic acids are the cheap and readily
prepared chemical materials. In 2013, a Cu/Ag co-catalyzed double-decarboxylative
coupling method for C-C bond formation was initially reported by Mai and
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
ACS Paragon Plus Environment

Page 3 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
9
co-workers.15 Nevertheless, to the best of our knowledge, the direct
double-decarboxylative cross-coupling of α-keto acids with cinnamic acids to form
C-C bonds has never been exploited.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Chalcones as the biologically active molecules are ubiquitous in natural products,
and widely used as the important building blocks in the organic transformations.16
However, literature survey indicated that the synthetic methods for the construction of
chalcone skeletons are rare. The traditional methods for chalcones synthesis are
mainly focus on the Claisen-Schmidt reactions.17 In 2013, Masahiro Miura and
Tetsuya Satoh described the decarboxylative arylation of 3-acylacrylic acids for the
synthesis of chalcones in the presence of palladium catalysis.18 Very recently, Su’
group developed an elegant palladium-catalyzed decarboxylative coupling between
aryl carboxylic acids and saturated propiophenones to access to chalcones.19 However,
it remains a challenging but attractive task to develop more practical and
environmentally-benign approaches for the synthesis of the useful chalcone
derivatives.
In view of green chemistry, water as an ideal reaction media with
environmentally benign and nontoxic characters has been attracting considerable
attentions. Besides that, water has been proven to affect the selectivity of lots of
organic reactions and to enhance the reaction rates.20 Herein, we report a novel and
efficient strategy for the construction of chalcones via silver-catalyzed
double-decarboxylative cross coupling of α-keto acids with cinnamic acids in water
(Scheme 1).
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 4 of 22
1
2
3
4
5
6
7
Scheme 1. Strategy to chalcones via decarboxylative reaction of α-keto acids with
cinnamic acids.
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
First, 2-oxo-2-phenylacetic acid (1a) and cinnamic acid (2a) were used as the
model substrates to screen the reaction conditions, including the oxidants, catalysts,
solvents and reaction temperatures under nitrogen atmosphere. As shown in Table 1,
three oxidants such as K2S2O8, Na2S2O8 and (NH4)2S2O8 were investigated at 50 oC by
using 0.1 equiv of AgNO3 as the catalyst, 2 equiv. of K2CO3 as the base in 2 mL
CH3CN/H2O (v1/v2=1:1), and Na2S2O8 gave the highest yield (21%) (entries 1-3), no
product was obtained in the absence of the oxidant (entry 15). The common silver
salts, AgNO3, Ag2CO3, Ag2O, and AgOAc were tested in CH3CN/H2O (entries 2, 4-6)
o
using Na2S2O8 as the oxidant at 50 C, and AgNO3 was observed to be the most
effective catalyst (entry 1, 4-6). Notably, the reaction was not proceed without the
catalyst (entry 14). We attempted to use different solvents (compare entries 1, 7-9),
and H2O was superior to the other solvents (entry 1). Moreover, various reaction
o
temperatures were examined (entries 9-12), and 100 C was discovered to be more
suitable for this reaction (entry 11). In addition, different amounts of K2CO3 were
employed in the reactions (compare entries 12 and 13), and the 2 equiv. of K2CO3
provided the highest yield (entry 12). After the optimization process of oxidants,
ACS Paragon Plus Environment

Page 5 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
9
catalysts, temperature and solvents, the various chalcone derivatives were synthesized
under the optimized conditions: 10 mol % AgNO3 as the catalyst, 1 equiv. of Na2S2O8
as the oxidant, 2 equiv. of K2CO3 as the base, and H2O as the solvent at 100 oC under
nitrogen atmosphere .
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Table 1. Sliver-catalyzed coupling reaction of 2-oxo-2-phenylacetic acid (1a) with
cinnamic acid (2b) leading to (E)-chalcone (3a): optimization of conditions.a
Entry
1
Cat.
Oxidant
K2S2O8
Solvent
CH3CN/H2O(1:1)
CH3CN/H2O(1:1)
CH3CN/H2O(1:1)
CH3CN/H2O(1:1)
CH3CN/H2O(1:1)
CH3CN/H2O(1:1)
dioxane/H2O(1:1)
acetone/H2O(1:1)
H2O
Temp. [oC] Yield [%]b
AgNO3
AgNO3
AgNO3
Ag2CO3
Ag2O
AgOAc
AgNO3
AgNO3
AgNO3
AgNO3
AgNO3
AgNO3
AgNO3
--
50
50
50
13
21
16
9
2
3
4
5
6
7
8
9
10
11
12
13
14
15
Na2S2O8
(NH4)2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
--
50
50
8
50
50
50
50
11
25
16
39
0
H2O
H2O
H2O
H2O
H2O
H2O
25
80
51
62
49c
0
100
100
100
100
AgNO3
0
a Reaction conditions: 2-oxo-2-phenylacetic acid (1a) (0.24 mmol), cinnamic acid (2a) (0.2 mmol),
catalyst (0.02 mmol), oxidant (0.1mmol), K2CO3(0.4 mmol), solvent (1.0 mL), reaction time (24 h)
under nitrogen atmosphere. b Isolated yield. c In the presence of K2CO3 (1 equiv).
As shown in Table 2, the scope and generality of this reaction was investigated
under the optimized conditions. As expected, a series of chalcones could be efficiently
obtained by this developed double-decarboxylative reaction. Generally, cinnamic
acids with electron-donating or withdrawing groups on the aryl ring could be
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 6 of 22
1
2
3
4
5
Table 2. Sliver-catalyzed synthesis of chalcone derivatives via decarboxylative
coupling of α-keto acids with cinnamic acids a,b,c
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
a
Reaction conditions: under nitrogen atmosphere, substituted α-keto acids (0.6 mmol), cinnamic
b
acids (0.5 mmol), AgNO3(0.05 mmol), K2S2O8 (0.25 mmol), CH3CN/H2O(v1/v2=1:1) (2.0 mL).
Isolated yield. c Reaction time (24 h).
smoothly transformed into the chalcones in moderate to good yields (Table 2, 3a-3t).
Cinnamic acids with the electron donating group, such as methoxy and methyl group
ACS Paragon Plus Environment

Page 7 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
9
could give good yields as compared to the cinnamic acids with the electron
withdrawing substituents. Furthermore, the effects of the substituent on α-keto acids
was investigated. The catalytic efficiency was not obviously affected by steric
hindrance in α-keto acids (Table 2, 3f, 3g and 3p-3r). Unfortunately, the α-keto acids
bearing strong electron-withdrawing groups, and aliphatic ones were the poor
coupling partners in this new transformation (Table 2, 3u-3w). Besides that, aliphatic
conjugated acids, such as crotonic acid did not work in the reaction (Table 2, 3x). The
silver-catalyzed double-decarboxylative reactions could tolerate some functional
groups such as C-Cl bonds, C-Br bonds and alkyl group which could be used for
further transformations.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Scheme 2. Investigations on the mechanism
To investigate the mechanism further, the coupling of 2-oxo-2-phenylacetic acid
(1a) with cinnamic acid (2a) was tested in the presence of a radical inhibitor, such as
TEMPO (2,2,6,6-tetramethylpiperidine 1-oxy). The formation of 3a was completely
inhibited in the reaction [Eq. (1). Scheme 2], thereby indicating that a radical process
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 8 of 22
1
2
3
4
5
6
7
8
9
might be involved. Treatment of benzaldehyde (4a) with 2-oxo-2-phenylacetic acid
(2a) did not afford the product (3a) [Eq. (2). Scheme 2]. Besides that, the desired
product (3a) was not observed when the reaction of 2-oxo-2-phenylacetic acid (1a)
with styrene (5a) under the standard conditions [Eq. (3). Scheme 2]. These
preliminary results indicated that benzaldehyde (4a) and styrene (5a) might not be the
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
important intermediates in the present transformations.
Scheme 3. Possible mechanism for the synthesis of chalcones
On the basis of these experimental results above, together with literature reports,21
we proposed the tentative mechanism in Scheme 3. Firstly, Ag(I) cation was oxidized
to Ag(II) cation by peroxodisulfate. Then, α-keto acids anion A reacted with the Ag(II)
cation to generate acyl radical B with releasing one molecular CO2 and Ag(I) cation.
Subsequently, the addition of acyl radical B to the α-position of the double bond of
cinnamate anion C leading to the formation of intermediate D. Finally, followed by
the loss of carbon dioxide and Ag(I) cation resulted in the chalcone products E.
ACS Paragon Plus Environment

Page 9 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
9
In summary, a novel and efficient protocol has been initially developed for the
synthesis of chalcone derivatives via silver-catalyzed decaroxylative coupling of
readily prepared α-keto acids and cinnamic acids in water. A series of chalcone
frameworks could be efficiently obtained in moderate to good yields under the mild
aqueous conditions.The easy and efficient approach could extend the scope of
synthetic methods for the preparation of diverse chalcones and it would attract much
attention in synthetic and pharmaceutical chemistry.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
EXPERIMENTAL SECTION
General.
All commercially available reagent and chemicals were purchased from chemical
1
13
suppliers and used as received without further purification. H NMR and C NMR
1
spectra were recorded in CDCl3 with TMS as internal standard (400 MHz H, 100
MHz 13C) at room temperature. Mass analyses and HRMS were obtained by ESI on a
TOF mass analyzer.. Column chromatography was performed on silica gel (200-300
mesh).
General experimental procedures.
A 25 mL Schlenk tube was charged with AgNO3 (8.5 mg, 0.05 mmol), potassium
carbonate (69 mg, 1.0 mmol), α-keto acids (0.6 mmol), cinnamic acids (0.5 mmol).
After the reaction vessel was evacuated thrice and backfilled with nitrogen, 2 mL
CH3CN/H2O(v1/v2=1:1) was added to the solution by syringe under a stream of
nitrogen. The tube was sealed and then the mixture was stired under at 100 oC for 24 h.
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 10 of 22
1
2
3
4
5
6
7
8
9
After completion of the reaction determined by TLC, the reaction solution was cooled
down to room temperature, then the mixture was extracted with ethyl acetate or
dichloromethane (3×4 mL). The combined organic phase was concentrated by a rotary
evaporator, and the residue was purified by column chromatography on silica gel
(200-300 mesh) to provide the desired product (3).
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
18
(E)-chalcone (3a): Following the general procedure, the product was isolated in
1
62% yield (64.5 mg). Eluent petroleum ether/ethyl acetate (30:1). H NMR (CDCl3,
400 MHz, ppm) δ 8.05 (d, 2H, J = 8.0 Hz), 7.84 (d, 2H, J = 16.0 Hz), 7.68 (dd, 2H, J
= 8.0 Hz), 7.62-7.52 (m, 4H), 7.46-7.44 (m, 3H). 13C NMR (CDCl3, 100 MHz, ppm) δ
190.6, 144.85, 134.93, 132.8, 130.6, 128.9, 128.6, 128.5, 128.4, 122.1. HRMS m/z
calcd. for C15H12O [M+H]+: 209.0966, found: 209.0965.
(E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (3b):22 Following the general
procedure, the product was isolated in 68% yield (82.3 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 8.04 (d, 2H, J = 8.0
Hz), 7.79 (d, 2H, J = 16.0 Hz), 7.63-7.60 (m, 3H), 7.56-7.52 (m, 3H), 7.42 (d, 2H, J =
8.0 Hz). 13C NMR (CDCl3, 100 MHz, ppm) δ 190.3, 143.3, 138.1, 136.5, 133.4, 132.9,
129.6, 129.3, 128.7, 128.5, 122.5. HRMS m/z calcd. for C15H11ClO [M+H]+:
243.0577, found: 243.0569.
(E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (3c):23 Following the general
procedure, the product was isolated in 75% yield (89.2 mg). Eluent petroleum
1
ether/ethyl acetate (30:1). H NMR (CDCl3, 400 MHz, ppm) δ 8.04 (d, 2H, J = 8.0
ACS Paragon Plus Environment

Page 11 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
9
Hz), 7.80 (d, 2H, J = 16.0 Hz), 7.62 (t, 1H, J = 8.0 Hz), 7.55 (s, 1H), 7.53 (d, 2H, J =
8.0 Hz), 7.37 (t, 1H, J = 8.0 Hz), 7.27 (d, 1H, J = 8.0 Hz), 7.18 (s, 1H), 3.89 (s, 3H).
13C NMR (CDCl3, 100 MHz, ppm) δ 190.6, 160.0, 144.8, 138.2, 136.3, 132.8, 130.0,
128.6, 128.5, 122.5, 121.1, 116.3, 113.5, 55.4. HRMS m/z calcd. for C16H14O2
[M+H]+: 239.1072, found: 239. 1068.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (3d):24 Following the general
procedure, the product was isolated in 80% yield (95.2 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 8.07 (d, 2H, J = 8.0
Hz), 7.83 (d, 1H, J = 16.0 Hz), 7.67 (dd, 2H, J = 8.0 Hz), 7.57 (d, 1H, J = 16.0 Hz),
7.45-7.43 (m, 2H), 7.82 (d, 2H, J = 8.0 Hz), 3.92 (s, 3H). 13C NMR (CDCl3, 100 MHz,
ppm) δ 188.8, 163.5, 144.0, 135.1, 131.1, 130.8, 130.3, 128.9, 128.4, 121.9, 113.9,
55.5. HRMS m/z calcd. for C16H14O2 [M+H]+: 239.1072, found: 239.1068.
(E)-3-(3-methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (3e):25 Following
the general procedure, the product was isolated in 86% yield (115.2 mg). Eluent
petroleum ether/ethyl acetate (20:1). 1H NMR (CDCl3, 400 MHz, ppm) δ 7.96 (d, 2H,
J = 8.0 Hz), 7.67 (d, 1H, J = 16.0 Hz), 7.46 (d, 1H, J = 16.0 Hz), 7.26-7.21 (m, 1H),
7.15 (d, 2H, J = 8.0 Hz), 7.08 (s, 1H), 6.90-6.85 (m, 3H), 3.79 (s, 3H) , 3.76 (s, 3H).
13C NMR (CDCl3, 100 MHz, ppm) δ 188.4, 170.8, 163.4, 159.9, 143.7, 136.4, 131.0,
130.7, 129.8, 122.1, 120.9, 116.0, 113.7, 113.3, 55.3, 55.1. HRMS m/z calcd. for
C17H16O3 [M+H]+: 269.1178, found: 269.1171.
(E)-1-(2,4-dimethoxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one
(3f):
Following the general procedure, the product was isolated in 90% yield (134 mg).
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 12 of 22
1
2
3
4
5
1
Eluent petroleum ether/ethyl acetate (30:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.78
6
7
8
9
(d, 2H, J = 8.0 Hz), 7.66 (d, 1H, J = 16.0 Hz ), 7.51 (d, 1H, J = 16.0 Hz ), 7.33 (t, 1H,
J = 8.0 Hz), 7.20 (d, 2H, J = 8.0 Hz), 7.14 (s, 1H), 6.95 (d, 2H, J = 8.0 Hz), 6.59 (dd,
1H, J = 8.0 Hz), 6.52 (s, 1H), 3.92 (s, 3H) , 3.89(s, 3H), 3.86(s, 3H). 13C NMR
(CDCl3, 100 MHz, ppm) δ 190.5, 164.2, 160.5, 160.0, 141.9, 137.0, 132.9, 129.8,
127.6, 122.2, 120.9, 115.6, 113.5, 105.3, 98.7, 55.8, 55.6, 55.3. HRMS m/z calcd. for
C18H18O4 [M+H]+: 299.1283, found: 299.1276.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(E)-1-(2,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3g):26
Following the general procedure, the product was isolated in 92% yield (164.6 mg).
1
Eluent petroleum ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.76
(d, 2H, J = 8.0 Hz), 7.59 (d, 1H, J = 16.0 Hz ), 7.39 (d, 1H, J = 16.0 Hz ), 6.85 (s, 2H),
13
6.59 (d, 2H, J = 8.0 Hz), 6.53 (s, 1H), 3.92-3.90 (m, 15H). C NMR (CDCl3, 100
MHz, ppm) δ 190.6, 164.1, 160.3, 153.4, 142.3, 132.7, 131.0, 126.7, 122.3, 105.6,
105.2, 98.8, 60.9, 56.2, 55.8, 55.6. HRMS m/z calcd. for C20H22O6 [M+H]+: 359.1495,
found: 359.1489
(E)-1-(naphthalen-2-yl)-3-phenylprop-2-en-1-one (3h):27 Following the general
procedure, the product was isolated in 80% yield (103.2 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 8.35 (d, 1H, J = 8.0
Hz), 7.03 (d, 1H, J = 8.0 Hz ), 7.95 (d, 1H, J = 8.0 Hz ), 7.62-7.57 (m, 6H), 7.44-7.42
(m, 3H), 7.34 (d, 1H, J = 16.0 Hz), 6.53 (s, 1H), 3.92-3.90 (m, 15H). 13C NMR
(CDCl3, 100 MHz, ppm) δ 195.8, 146.0, 137.1, 134.7, 133.9, 131.6, 130.7, 130.5,
129.0, 128.5, 128.4, 127.5, 127.2, 127.1, 126.5, 125.7, 124.5. HRMS m/z calcd. for
ACS Paragon Plus Environment

Page 13 of 22
The Journal of Organic Chemistry
1
2
3
4
5
C19H14O [M+H]+: 259.1123, found: 259.1121.
6
7
8
9
(E)-3-(4-chlorophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one (3i):27 Following the
general procedure, the product was isolated in 78% yield (113.8 mg). Eluent
petroleum ether/ethyl acetate (10:1). 1H NMR (CDCl3, 400 MHz, ppm) δ 8.36 (d, 1H,
J = 8.0 Hz), 8.03 (d, 1H, J = 8.0 Hz ), 7.94 (d, 1H, J = 8.0 Hz ), 7.80 (d, 1H, J = 8.0
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
13
Hz ), 7.61-7.51 (m, 6H), 7.39 (d, 1H, J = 8.0 Hz ), 7.30 (d, 1H, J = 16.0 Hz). C
NMR (CDCl3, 100 MHz, ppm) δ 195.3, 144.3, 137.1, 136.9, 136.6, 133.9, 133.2,
131.8, 130.5, 129.6, 129.3, 128.5, 127.6, 127.5, 127.2, 126.6, 125.6, 124.5. HRMS
m/z calcd. for C19H13ClO [M+H]+: 293.0733, found: 293.0730.
(E)-3-(4-bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one (3j):27 Following the
general procedure, the product was isolated in 75% yield (126.0 mg). Eluent
petroleum ether/ethyl acetate (10:1). 1H NMR (CDCl3, 400 MHz, ppm) δ 8.36 (d, 1H,
J = 8.0 Hz), 8.03 (d, 1H, J = 8.0 Hz ), 7.94 (d, 1H, J = 8.0 Hz ), 7.60-7.55 (m, 6H),
7.46 (d, 1H, J = 8.0 Hz ), 7.31 (d, 1H, J = 16.0 Hz). 13C NMR (CDCl3, 100 MHz, ppm)
δ 195.3, 144.3, 136.9, 133.9, 133.6, 132.3, 131.8, 130.8, 130.5, 129.8, 128.8, 128.5,
127.6, 127.2, 126.6, 125.6, 125.0, 124.5. HRMS m/z calcd. for C19H13BrO [M+H]+:
336.0150, 338.0129, found: 336.0155, 338.0136.
(E)-1-(naphthalen-2-yl)-3-p-tolylprop-2-en-1-one (3k):28 Following the general
procedure, the product was isolated in 82% yield (111.5 mg). Eluent petroleum
1
ether/ethyl acetate (10:1). H NMR (CDCl3, 400 MHz, ppm) δ 8.33 (d, 1H, J = 8.0
Hz), 8.02 (d, 1H, J = 8.0 Hz ), 7.78 (d, 1H, J = 8.0 Hz ), 7.62-7.54 (m, 4H), 7.50 (d,
2H, J = 8.0 Hz ), 7.30 (d, 1H, J = 16.0 Hz), 7.23 (d, 2H, J = 8.0 Hz), 2.41 (s, 3H). 13C
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 14 of 22
1
2
3
4
5
6
7
8
9
NMR (CDCl3, 100 MHz, ppm) δ 196.0, 146.2, 141.3, 137.3, 133.9, 131.9, 131.4,
130.5, 129.7, 128.8, 128.5, 128.4, 127.4, 127.0, 126.3, 125.7, 124.5, 21.5. HRMS m/z
calcd. for C20H16O [M+H]+: 273.1279, found: 273.1282.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(E)-3-(3-methoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one (3l):29 Following the
general procedure, the product was isolated in 71% yield (102.2 mg). Eluent
petroleum ether/ethyl acetate (20:1). 1H NMR (CDCl3, 400 MHz, ppm) δ 8.36 (d, 1H,
J = 8.0 Hz), 8.03 (d, 1H, J = 8.0 Hz ), 7.94 (d, 1H, J = 8.0 Hz ), 7.80 (d, 1H, J = 8.0
Hz ), 7.62-7.55 (m, 4H), 7.36-7.30 (m, 2H), 7.20 (d, 1H, J = 8.0 Hz ), 7.12 (s, 1H),
13
7.69 (d, 2H, J = 8.0 Hz), 3.85 (s, 3H). C NMR (CDCl3, 100 MHz, ppm) δ 195.6,
160.0, 145.9, 137.1, 136.0, 133.8, 131.6, 130.5, 130.0, 128.5, 127.5, 127.4, 127.2,
126.5, 125.7, 124.5, 121.2, 116.7, 113.3, 55.4. HRMS m/z calcd. for C20H16O2
[M+H]+: 289.1229, found: 289.1232.
(E)-3-(3-methoxyphenyl)-1-m-tolylprop-2-en-1-one (3m): Following the general
procedure, the product was isolated in 78% yield (98.3 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 8.85-7.83 (m, 2H),
7.79 (d, 1H, J = 16.0 Hz ), 7.53 (d, 1H, J = 16.0 Hz ), 7.43-7.41 (m, 2H), 7.36 (t, 1H,
J = 8.0 Hz ), 7.28-7.26 (m, 2H), 7.19 (s, 1H), 6.99 (d, 2H, J = 8.0 Hz), 3.88 (s, 3H),
13
2.47 (s, 3H). C NMR (CDCl3, 100 MHz, ppm) δ 190.7, 160.0, 144.6, 138.5, 138.3,
136.4, 133.6, 130.0, 129.1, 128.5, 125.7, 122.6, 121.1, 116.2, 113.5, 55.4, 21.4.
HRMS m/z calcd. for C17H16O2 [M+H]+: 253.1229, found: 253.1219.
(E)-1, 3-dip-tolylprop-2-en-1-one (3n):30 Following the general procedure, the
product was isolated in 72% yield (84.9 mg). Eluent petroleum ether/ethyl acetate
ACS Paragon Plus Environment

Page 15 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
(20:1). 1H NMR (CDCl3, 400 MHz, ppm) δ 7.84 (d, 2H, J = 8 Hz), 7.65 (d, 1H, J = 16
Hz), 7.34 (d, 2H, J = 8 Hz), 7.32-7.29 (m, 3H), 6.85 (d, 1H, J = 16 Hz), 2.46 (s, 3H),
7
8
9
13
2.37 (s, 3H). C NMR (CDCl3, 100 MHz, ppm) δ 190.1, 144.3, 142.2, 138.8, 137.9,
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
132.4, 131.9, 129.9, 129.1, 128.9, 127.7, 127.4, 125.8, 21.6, 21.3. HRMS m/z calcd.
for C17H16O [M+H]+: 273.1279, found: 273.1279.
(E)-3-(4-chlorophenyl)-1-p-tolylprop-2-en-1-one (3o):31 Following the general
procedure, the product was isolated in 66% yield (79.4 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.96 (d, 2H, J = 8.0
Hz ), 7.77 (d, 1H, J = 16.0 Hz ), 7.60 (d, 2H, J = 8.0 Hz ), 7.53 (d, 1H, J = 16.0 Hz ),
13
7.41 (d, 2H, J = 8.0 Hz ), 7.33 (d, 2H, J = 8.0 Hz ), 2.47 (s, 3H). C NMR (CDCl3,
100 MHz, ppm) δ 189.7, 143.9, 142.9, 136.3, 135.5, 133.5, 129.6, 129.4, 129.2, 128.7,
122.5, 21.7. HRMS m/z calcd. for C16H13ClO [M+H]+: 257.0733, found: 257.0726.
(E)-3-(4-chlorophenyl)-1-o-tolylprop-2-en-1-one (3p):32 Following the general
procedure, the product was isolated in 54% yield (69.1 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.52-7.51 (m, 3H),
7.47-7.39 (m, 4H), 7.31 (d, 1H, J = 8.0 Hz ), 7.14 (d, 1H, J = 16.0 Hz ), 2.47 (s, 3H).
13C NMR (CDCl3, 100 MHz, ppm) δ 196.1, 144.2, 138.9, 137.1, 136.6, 133.2, 131.4,
130.6, 129.6, 129.3, 128.1, 127.1, 125.5, 20.3. HRMS m/z calcd. for C16H13ClO
[M+H]+: 257.0733, found: 257.0726.
(E)-3-(3-chlorophenyl)-1-o-tolylprop-2-en-1-one (3q): Following the general
procedure, the product was isolated in 64% yield (82.0 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.57 (s, 1H), 7.53 (d,
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 16 of 22
1
2
3
4
5
1H, J = 8.0 Hz), 7.47-7.41 (m, 3H), 7.39-7.21 (m, 4H), 7.15 (d, 1H, J = 16.0 Hz)
6
7
13
2.48 (s, 3H). C NMR (CDCl3, 100 MHz, ppm) δ 195.9, 143.9, 138.7, 137.2, 136.5,
8
9
135.0, 131.5, 130.8, 130.4, 130.2, 128.2, 128.1, 127.8, 126.6, 125.6, 20.3. HRMS m/z
calcd. for C16H13ClO [M+H]+: 257.0733, found: 257.0726.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(E)-3-(4-fluorophenyl)-1-o-tolylprop-2-en-1-one (3r): Following the general
procedure, the product was isolated in 66% yield (79.2 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.60-7.56 (m, 2H),
7.53-7.39 (m, 3H), 7.29 (d, 2H, J = 8.0 Hz), 7.14-7.07 (m, 3H), 2.47 (s, 3H). 13C
NMR (CDCl3, 100 MHz, ppm) δ 196.3, 165.4, 162.9, 144.5, 140.1, 139.0, 131.6,
131.4, 130.5, 130.3(d, J = 160 Hz), 128.1, 127.4, 126.5(d, J = 12 Hz), 125.8, 125.5,
116.3, 116.1, 20.2. HRMS m/z calcd. for C16H13FO [M+H]+: 241.1029, found:
241.1032.
(E)-1-o-tolyl-3-p-tolylprop-2-en-1-one (3s): Following the general procedure, the
product was isolated in 69% yield (81.4 mg). Eluent petroleum ether/ethyl acetate
1
(20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.51-7.38 (m, 5H), 7.31-7.29 (m, 2H),
13
7.23 (d, 2H, J = 8.0 Hz), 7.11(d, 2H, J = 16.0 Hz), 2.46 (s, 3H), 2.41 (s, 3H). C
NMR (CDCl3, 100 MHz, ppm) δ 196.8, 146.1, 141.2, 139.3, 136.8, 131.9, 131.3,
130.3, 129.7, 128.5, 128.0, 125.9, 125.4, 21.5, 20.1. HRMS m/z calcd. for C17H16O
[M+H]+: 237.1279, found: 237.1280.
(E)-3-(3-methoxyphenyl)-1-o-tolylprop-2-en-1-one (3t): Following the general
procedure, the product was isolated in 75% yield (94.5 mg). Eluent petroleum
1
ether/ethyl acetate (20:1). H NMR (CDCl3, 400 MHz, ppm) δ 7.52 (d, 2H, J = 8.0
ACS Paragon Plus Environment

Page 17 of 22
The Journal of Organic Chemistry
1
2
3
4
5
Hz), 7.45 (d, 1H, J = 16.0 Hz), 7.38 (d, 2H, J = 8.0 Hz), 7.36-7.30 (m, 3H), 7.19-7.10
6
7
13
(m, 3H), 6.69 (d, 1H, J = 8.0 Hz), 3.86 (s, 3H), 2.47 (s, 3H). C NMR (CDCl3, 100
8
9
MHz, ppm) δ 196.6, 160.0, 145.8, 139.1, 137.0, 136.0, 131.3, 130.5, 130.0, 128.1,
127.1, 125.5, 121.1, 116.6, 113.2, 55.3, 20.2. HRMS m/z calcd. for C17H16O2 [M+H]+:
253.1229, found:253.1226.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
ASSOCIATED CONTENT
Supporting Information
Spectral data for all compounds. This material is available free of charge via the
Internet at http://pubs.acs.org/.
AUTHOR INFORMATION
Corresponding Author
* E-mail: yangdaoshan@tsinghua.org.cn
* E-mail: huawang_qfnu@126.com
Notes
The authors declare no competing financial interest.
ACKNOWLEGEMENTS
The authors gratefully acknowledge the financial support from the National Natural
Science Foundation of China (Nos. 21302110, 21302109 and 21375075), the Taishan
Scholar Foundation of Shandong Province, the Natural Science Foundation of
Shandong Province (ZR2013BQ017 and ZR2013M007), the Project of Shandong
Province Higher Educational Science and Technology Program (J13LD14).
REFERENCES
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 18 of 22
1
2
3
4
5
6
7
8
9
(1) (a) Corey, E. J.; Cheng, X. M. The Logic of Chemical Synthesis; John Wiley &
Sons: New York, 1989; pp 1-91. (b) Suzuki, A. In Metal-Catalyzed
Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH:
Weinheim, Germany, 1998; p 49-89.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(2) (a) Li, C.-J. Chem. Rev. 2005, 105, 3095-3165. (b) Beccalli, E. M.; Broggini, G.;
Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318-5365.
(3) (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11-59. (b) Knochel, P.; Singer, R.
Chem. Rev. 1993, 93, 2117-2188. (c) Negishi, E. I. Acc. Chem. Res. 1982, 15,
340-348. (d) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846.
(4) (a) Goossen, L. J.; Deng, G.; Levy, L. M. Science. 2006, 313, 662-664. (b)
Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J.
Am. Chem. Soc. 2007, 129, 4824-4833. (c) Goossen, L. J.; Rodríguez, N.; Gooßen,
K. Angew. Chem. Int. Ed. 2008, 47, 3100-3120. (d) Goossen, L. J.; Rodríguez, N.;
Linder, C. J. Am. Chem. Soc., 2008, 130, 15248-15249. (e) Goossen, L. J.; Lange,
P. P.; Rodríguez, N.; Linder, C. Chem. Eur. J. 2010, 16, 3906-3909. (f) Tang, J.;
Gooßen, L. J. Org. Lett. 2014, 16, 2664-2667. (g) Dzik, W. I.; Lange, P. P.;
Gooßen, L. J. Chem. Sci. 2012, 3, 2671-2678. (h) Lange, P. P.; Goossen, L. J.;
Podmore, P.; Underwood, T.; Sciammetta, N. Chem. Commun. 2011, 47,
3628-3630. (i) Song, B.; Knauber, T.; Goossen, L. J. Angew. Chem. Int. Ed. 2013,
52, 2954-2958.
(5) (a) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127,
10323-10333. (b) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc.
ACS Paragon Plus Environment

Page 19 of 22
The Journal of Organic Chemistry
1
2
3
4
5
2002, 124, 11250-11251.
6
7
8
9
(6) For selected examples, see: (a) Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen,
K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350-11351. (b)
Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006-14008. (c)
Satoh, T.; Miura, M. Synthesis. 2010, 3395-3409. (d) Jafarpour, F.; Zarei, S.; Olia,
M. B. A.; Jalalimanesh, N.; Rahiminejadan, S. J. Org. Chem. 2013, 78, 2957-2964.
(e) Zhang, F.; Greaney, M. F. Org. Lett. 2010, 12, 4745-4747. (f) Neely, J. M.;
Rovis, T. J. Am. Chem. Soc. 2014, 136, 2735-2738. (g) Shang, R.; Yang, Z.-W.;
Wang, Y.; Zhang, S.-L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391-14393. (h)
Li, C.; Breit, B. J. Am. Chem. Soc. 2014, 136, 862-865.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(7) (a)Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030-5048. (b) Zhang,
Y.; Patel, S.; Mainolfi, N. Chem. Sci. 2012, 3, 3196-3199. (c) Weaver, J. D.; Recio,
A., III; Grenning, A. J.;Tunge, J. A. Chem. Rev. 2011, 111, 1846-1913. (d)
Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodr_guez, N. Angew. Chem. Int. Ed.
2008, 47, 3043-3045.
(8) Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem. Int.
Ed. 2014, 53, 502-506.
(9) (a) Wang, H.; Guo, L.-N.; Duan, X.-H. Chem. Commun. 2014, 50, 7382-7384. (b)
Wang, H.; Guo, L.-N.; Duan, X.-H, Adv. Synth. Catal. 2013, 355, 2222-2226.
(10) (a) Fang, P.; Li, M.; Ge, H. J. Am. Chem. Soc. 2010, 132, 11898-11899. (b) Kim,
M.; Park, J.; Sharma, S.; Kim, A.; Park, E.; Kwak, J. H.; Jung, Y. H.; Kim, I. S.
Chem. Commun. 2013, 49, 925-927. (c) Wang, H.; Guo, L.-N.; Duan, X.-H. Org.
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 20 of 22
1
2
3
4
5
6
7
Lett. 2012. 14. 4358-4361. (d) Li, Z.-Y.; Li, D.-D.; Wang, G.-W. J. Org. Chem.
2013, 78, 10414-10420.
8
9
(11) (a) Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 592-595.
(b) Wang, Z.; Ding, Q.; He, X.; Wu, J. Org. Biomol. Chem. 2009, 7, 863-865.
(12) (a) Yang, H.; Sun, P.; Zhu, Y.; Yan, H.; Lu, L.; Qu, X.; Li, T.; Mao, J. Chem.
Commun. 2012, 7847-7849. (b) Cui, Z.; Shang, X.; Shao, X.-F.; Liu, Z.-Q. Chem.
Sci. 2012, 3, 2853-2858. (c) Li, Z.; Cui, Z.; Liu, Z.-Q. Org. Lett. 2013, 15,
406-409. (d) Rong, G.; Liu, D.; Lu, L.; Yan, H.; Zheng, Y.; Chen, J.; Mao, J.
Tetrahedron. 2014, 70, 5033-5037. (e) Zhao, J.; Fang, H.; Han, J.; Pan, Y.
Beilstein J. Org.Chem. 2013, 9, 1718-1723.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(13) Manna, S.; Jana, S.; Saboo, T.; Maji, A.; Maiti, D. Chem. Commun. 2013,
5286-5288.
(14) (a) Xu, Y.; Tang, X.; Hu, W.; Wu, W.; Jiang, H. Green Chem. 2014, 16,
3720-3723. (b) Rokade, B. V.; Prabhu, K. R. J. Org.Chem. 2014, 79, 8110-8117.
(c) Li, H.-S.; Liu, G. J. Org. Chem. 2014, 79, 509-516.
(15) Mai, W.-P.; Song, G.; Sun, G.-C.; Yang, L.-R.; Yuan, J.-W.; Xiao,Y.-M.; Mao, P.;
Qu, L.-B. RSC Adv. 2013, 3, 19264-19267.
(16) (a) Nowakowska, Z. Eur. J. Med. Chem. 2007, 42, 125-137. (b) Cabrera, M.;
Simoens, M.; Falchi, G.; Lavaggi, M. L.; Piro, O. E.; Castellano, E. E.; Vidal, A.;
Azqueta, A.; Monge, A.; Lopez, A.; Sagrera, G.; Seoane, G.; Cerecetto, H.;
Gonzalez, M.; Bioorg. Med. Chem. 2007, 15, 3356-3367. (c) Rao, Y. K.; Fang,
S.-H.; Tzeng, Y.-M. Bioorg. Med. Chem. 2004, 12, 2679-2686. (d) Liu, M.;
ACS Paragon Plus Environment

Page 21 of 22
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
9
Wilairat, P.; Croft, S. L.; Tan, A. L.-C.; Go, M.-L. Bioorg. Med. Chem. 2003, 11,
2729-2738. (e) Weber, W. M.; L. Hunsaker, A. S.; Abcouwer, F.; Deck, L. M.;
Jagt, D. L. V. Bioorg. Med. Chem. 2005, 13, 3811-3820. (f) Anto, R. J.;
Sukumaran, K.; Kuttan, G.; Rao, M. N. A.; Subbaraju, V.; Kuttan, R. Cancer
Lett. 1995, 97, 33-37.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(17) (a) Choudary, B. M.; Kantam, M. L.; Ranganath, K. V. S.; Mahendar, K.;
Sreedhar, B. J. Am. Chem. Soc. 2004, 126, 3396-3397. (b) Fang, D., Cheng, J.;
Fei, Z.; Gong, K.; Liu, Z. Catal. Commun. 2008, 9, 1924-1927.
(18) Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013, 78, 5096-5102.
(19) Zhou, J.; Wu, G.; Zhang, M.; Jie, X.; Su, W. Chem. Eur. J. 2012, 18, 8032-8036.
(20) Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725-748.
(21) (a) Anderson, J. M.; Kochi, J. K. J. Am. Chem. Soc. 1970, 92, 1651-1653. (b)
Fontana, F.; Minisci, F.; Claudia, M.; Barbosa, N.; Vismara, E. J. Org. Chem.
1991, 56, 2866-2869.
(22) Wang, P.; Liu, C.-R.; Sun, X.-L.; Chen, S.-S.; Li, J.-F.; Xie, Z.; Tang, Y. Chem.
Commun. 2012,48, 290-292 .
(23) Chang, M.-Y.; Tsai, C.-Y.; Wu, M.-H. Tetrahedron. 2013, 69, 6364-6370.
(24) Jacubert, M.; Provot, O.; Peyrat, J.-F.; Hamze, A.; Brion, J.-D.; Alami, M.
Tetrahedron. 2010, 66, 3775-3787.
(25) Kumar, A.; Sharma, S.; Tripathi, V. D.; Srivastava, S. Tetrahedron. 2010, 66,
6445-9449.
ACS Paragon Plus Environment

The Journal of Organic Chemistry
Page 22 of 22
1
2
3
4
5
(26) Bandgar, B. P.; Gawande, S. S.; Bodadec, R. G.; Totre, J. V.; Khobragad, C.
6
7
N. Bioorg & Med Chem. 2010, 18, 1364-1370.
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(27) Winter, E, Chiarad, L. D., Cordova, C. A. S., José Nunes, R., Yunes, R. A.,
Creczynski-Pasaa, T, B. Bioorg & Med Chem. 2010, 18, 8026-8034.
(28) Li, X.; Zou, D.; Leng, F.; Sun, C.; Li, J.; Wu, Y.; Wu, Y. Chem. Commun. 2013,
49, 312-314.
(29) Chang, M.-Y.; Chan, C.-K.; Lin, S.-Y.; Wu, M.-H. Tetrahedron. 2013, 69,
9616-9624.
(30) Yang, J.-X.; Tao, X.-T.; Yuan, C. ; Yan, Y.; Wang, L.; Liu, Z.; Ren, Y.; Jiang,
M. J. Am. Chem. Soc. 2005, 127, 3278-3279.
(31) Madapa, S.; Sridhar, D.; Yadav, G. P.; Maulik, P.- R.; Batra, S. Eur. J. Org. Chem.,
2007, 4343-4351.
(32) Cardia, M.-C.; Sanna, M.-L.; Meleddu, R.; Distinto, S.; Yañez, M.; Viña, D.;
Lamela, M.; Maccioni, E. J. Heterocyclic Chem., 2013, 50, E87-E92.
ACS Paragon Plus Environment