Nickel-catalyzed decarboxylative coupling of an alkynyl carboxylic acid with aryl iodides

Article abstract of DOI:10.1016/j.tetlet.2017.02.073

A decarboxylative coupling reaction with an alkynyl carboxylic acid and aryl iodides in the presence of a nickel catalyst was developed. When the reaction was conducted with NiCl₂ (10?mol%), Xantphos (15?mol%), Mn (1.0?equiv), and Cs₂CO₃ (1.5?equiv), the desired diaryl alkynes were formed in moderated to good yields. Furthermore, this method does not produce the diyne, which is formed in the homocoupling of alkynyl carboxylic acids.

Full text of DOI:10.1016/j.tetlet.2017.02.073

Accepted Manuscript
Nickel-Catalyzed Decarboxylative Coupling of an Alkynyl Carboxylic Acid
with Aryl Iodides
Yujeong Son, Han-Sung Kim, Ju-Hyeon Lee, Jisun Jang, Chin-Fa Lee, Sunwoo
Lee
PII:
S0040-4039(17)30260-5
DOI:
http://dx.doi.org/10.1016/j.tetlet.2017.02.073
TETL 48684
Reference:
Tetrahedron Letters
To appear in:
Received Date:
Revised Date:
Accepted Date:
30 November 2016
14 February 2017
24 February 2017
Please cite this article as: Son, Y., Kim, H-S., Lee, J-H., Jang, J., Lee, C-F., Lee, S., Nickel-Catalyzed
Decarboxylative Coupling of an Alkynyl Carboxylic Acid with Aryl Iodides, Tetrahedron Letters (2017), doi: http://
dx.doi.org/10.1016/j.tetlet.2017.02.073
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Tetrahedron Letters
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Nickel-Catalyzed Decarboxylative Coupling of an Alkynyl Carboxylic Acid with
Aryl Iodides
Yujeong Son,a Han-Sung Kim,a Ju-Hyeon Lee,a Jisun Jang,a Chin-Fa Lee,b* Sunwoo Leea*
aDepartment of Chemistry, Chonnam National University, Gwangju 61186, Republic of Korea
bDepartment of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, R.O.C
ARTICLE INFO
ABSTRACT
Article history:
Received
A decarboxylative coupling reaction with an alkynyl carboxylic acid and aryl iodides in the
presence of a nickel catalyst was developed. When the reaction was conducted with NiCl2 (10
mol%), Xantphos (15 mol%), Mn (1.0 equiv), and Cs2CO3 (1.5 equiv), the desired diaryl alkynes
were formed in moderated to good yields. Furthermore, this method does not produce the diyne,
which is formed in the homocoupling of alkynyl carboxylic acids.
Received in revised form
Accepted
Available online
2009 Elsevier Ltd. All rights reserved.
Keywords:
Nickel
Decarboxylative coupling
Alkynyl carboxylic acid
Aryl iodide
Reductant
Introduction
alkyne surrogates, and exhibit good activity in this reaction with
a variety of coupling partners.15 Furthermore, they can be readily
Transition metal–catalyzed cross-coupling reactions are
among the most important and widely used tools in organic
synthesis for the formation of carbon-carbon or carbon-
heteroatom bonds.1 A variety of named reactions, including the
Heck,2 Kumada,3 Negishi,4 Stille,5 Suzuki,6 Sonogashira,7
Hiyama,8 and Buchwald-Hartwig9 reactions, have been
developed and improved over the last four decades. As a
coupling substrate, aryl halides are the most commonly employed
because they are readily available. Generally, aryl iodides are
much more reactive than aryl bromides and chlorides.10
prepared in one step without the need for column
chromatography for purification.16
We have previously reported a number of decarboxylative
coupling reactions. For example, synthetic strategies for diaryl
alkynes, diynes, diketones, allenes, alkynyl ketones, and alkynyl
amides have been developed.17 In addition, several
multicomponent reactions have been developed.18 These
reactions are catalyzed by palladium or copper in most cases,
with only a few rare examples of nickel catalysts being reported,
even though it is more abundant and less expensive than
Sonogashira first showed that aryl halides are capable of
coupling with terminal alkynes in the presence of palladium,
copper, and a base to provide aryl alkynes. Since his first report
of this reaction in 1979, it has become the most common method
for sp and sp2 carbon bond formation, and is now known as the
Sonogashira reaction.11 It is very often employed as an useful
tool for the synthesis of conjugated polymers in the electroactive
material field.12 Palladium is used as the catalyst for this reaction
far more often than other transition metals such as copper and
nickel.13
palladium. The first example of
a
nickel-catalyzed
decarboxylative coupling reaction was that with an allyl acetate,
as shown in Figure 1a.19 Recently, we reported nickel-catalyzed
decarboxylative coupling reactions with aryl siloxanes or aryl
boronic acids (Figure 1b).20 These successes prompted us to
develop a nickel-catalyzed decarboxylative coupling reaction
with aryl halides, which has long been regarded as a challenge.
Herein, we report for the first time the nickel-catalyzed
decarboxylative coupling of an alkynyl carboxylic acid and aryl
iodides (Figure 1c).
As an alternative method, the decarboxylative coupling of
alkynyl carboxylic acids has received much attention since we
first reported the palladium-catalyzed coupling of alkynyl
carboxylic acids and aryl halides in 2008.14 Alkynyl carboxylic
acids such as propiolic acid have been widely employed as
--
Corresponding author. E-mail address: cfalee@dragon.nchu.edu.tw
(C.-F. Lee), sunwoo@chonnam.ac.kr (S.Lee)

2
Tetrahedron
9
Ni[P(C6H5)3]2
NiCl2
NiCl2
L1
L1
L1
L1
L1
L2
L3
L4
L1
L1
L1
K2CO3
Cs2CO3
Na2CO3
DBU
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMF
80
80
1
67
10
11
12
13
14
15
16
17
18
19
80
80
22
17
NiCl2
NiCl2
NiCl2
NiCl2
DBN
80
80
13
5
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
80
80
110
110
110
110
trace
trace
83
NiCl2
NiCl2
NiCl2
NiCl2
30
20
Toluene
Diglym
e
20
NiCl2
L1
Cs2CO3
51
21
22
23
24
25
26
Ni(acac)2
Ni(acac)2
Ni(acac)2
L2
L3
L4
L2
L3
L4
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
110
110
110
110
110
110
5
22
64
13
6
Figure 1. Nickel-catalyzed decarboxylative coupling reactions.
Ni(OAc)24H2O
Ni(OAc)24H2O
Ni(OAc)24H2O
9
aReaction Conditions: 1a (0.3 mmol), 2a (0.6 mmol), Ni (0.03 mmol), ligand
(0.045 mmol), Mn (0.3 mmol), and base (0.45 mmol) were reacted in solvent
(1.0 mL).
To optimize the reaction conditions, phenyl propiolic acid and
iodobenzene were chosen as standard substrates. A variety of
reaction parameters were investigated, as shown in Table 1. First,
we assessed a number of nickel sources. Generally, Ni(COD)2 is
the most frequently employed nickel source in cross-coupling
reactions with aryl halides. However, it is very air-sensitive and
thus difficult to handle and transport.21 Therefore, we employed
the much more stable nickel(II) as a nickel source in the presence
of manganese.22
Of the commercially available nickel complexes, only
Ni(OAc)2·4H2O and NiCl2 provide the coupled product,
achieving moderate yields of 44 and 48%, respectively (entries 3
and 4). When Cs2CO3 is employed as a base instead of K2CO3,
the product yield increases to 67% (entry 10); however, other
bases such as Na2CO3, DBU, and DBN result in poor yields
(entries 11–13). The reactions with other chelating phosphine
ligands such as DPEPhos (L2), BINAP (L3), and dppf (L4)
provide only trace amounts of the product (entries 14–16). When
the reaction temperature is increased to 110 °C, the desired
product is formed in 83% yield (entry 17). When the reaction is
run at 110 °C in DMF, toluene, or diglyme, the yields are not
satisfactory (entries 18–20).
Figure 2. Structures of the ligands L1–L4.
With the optimum conditions established, we investigated the
substrate scope of the reaction (Table 2). As expected, phenyl
iodide couples with phenyl propiolic acid to give diphenyl
acetylene (3a) in 88% yield (entry 1). The ortho-substituted
iodotoluene reacts with low yields in both NiCl2/Xantphos and
Ni(acac)2/dppf (entry 2), while the meta- and para-substituted
iodotoluenes afford the corresponding coupled products in 41 and
79% yields, respectively (entries 3 and 4). Iodoanisoles react at
low to moderate yields (entries 5 and 6). 4-Fluoro- and 4-chloro-
iodobenzene provide the desired products in 42 and 79% yields,
respectively (entries 7 and 8). 4-Iodopyridine couples with
phenyl propiolic acid to give 3i in 83% yield (entry 9). Methyl 4-
iodobenzoate and 1-iodonaphthalene give the desired products in
47 and 57% yields, respectively (entries 10 and 11). 1-Iodo-4-
(trifluoromethyl)benzene afforded 3l with 82% yield (entry 12).
4-Iodoacetophenone affords the desired product with 16% yield
in the presence of NiCl2/ Xantphos. However, when these
reactions are performed with Ni(acac)2/ dppf, it provide the
coupled product 3m in 39% yield, respectively (entry 13). Aryl
iodides bearing cyano or nitro groups do not afford the coupled
products under either set of conditions (entries 14 and 15).
We also investigated the reaction with different combinations
of nickel source and ligand (Figure 2). Three kinds of ligands
were tested with Ni(acac)2 in the presence of Cs2CO3 in DMSO.
DPEPhos, BINAP, and dppf afford 3a in 5, 22, and 64% yields,
respectively (entries 21–23). However, the use of
Ni(OAc)2·4H2O results in poor yields, irrespective of the
phosphine ligand employed (entries 24–26). It is noteworthy that
no homocoupled phenyl propiolic acid product, which is 1,4-
diphenyl-1,3-butadiyne, is observed in any of the reactions.
Table 1. Screening of Ni source, ligand, base, solvent, and
temperature for the decarboxylative coupling reaction.
Table 2. Ni-catalyzed decarboxylative coupling reactions between
aryl iodides and phenyl propiolic acid.a
Yield
(%)
3
Entry
Ni
Ligand
Base
Solvent
Temp
Yieldb
(%)
1
2
3
4
5
6
7
8
Ni(acac)2
Ni(NO3)26H2O
Ni(OAc)24H2O
NiCl2
L1
L1
L1
L1
L1
L1
L1
L1
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
80
80
80
80
80
80
80
80
1
Entry
1
ArI
Product
44
48
3
3a
88
NiF2
Ni(OH)2
4
Ni(Cp)2
NiBr2 glyme
1
1

Yieldb
(%)
Entry
1
Propiolic acids
Product
2
3b
20(27)c
1b
1c
3p
67
77
3
4
5
3c
3d
3e
41
79
2
3c
3
4
5
1d
1e
1f
3f
3h
3l
69
77
82
20(66)c
6
7
8
9
3f
3g
3h
3i
59
42
79
83
6
7
1g
1h
3p
3q
81
85
O
aReaction conditions: 1 (3.0 mmol), 2a (3.0 mmol), NiCl2 (0.3 mmol),
Xantphos (0.45 mmol), Mn (3.0 mmol), and Cs2CO3 (4.5 mmol) were reacted
in DMSO at 110 °C, 12 h. bIsolated Yield.
I
10
11
3j
47
57
MeO
3k
We attempted to expand this nickel-catalyzed decarboxylative
coupling reaction toward aryl bromide and chloride. However, no
product was formed.
12
13
3l
82(22)c
16(39)c
We have proposed a plausible mechanism for the reaction, as
shown in Scheme 1. Ni(II) is reduced to Ni(0) in the presence of
manganese.23 The aryl iodide reacts with Ni(0) to give the
oxidative addition complex A. The phenyl propiolic acid salt,
which is formed by the reaction with Cs2CO3, reacts with nickel
complex A to provide the aryl alkynyl nickel complex B through
a decarboxylative ligand exchange reaction. Finally, reductive
elimination affords the desired coupled product and Ni(0).
O
I
3m
Me
NC
14
15
3n
3o
0
0
I
aReaction conditions: 1 (3.0 mmol), 2 (3.0 mmol), NiCl2 (0.3 mmol),
Xantphos (0.45 mmol), Mn (3.0 mmol), and Cs2CO3 (4.5 mmol) were
reacted in DMSO at 110 °C, 12 h. bIsolated Yield. cNi(acac)2 (0.3 mmol) and
dppf (0.3 mmol) were used instead of NiCl2/Xantphos.
Ar
X
Ar
Ph
Ni
Ni(0)
To further evaluate this methodology, substituted aryl
propiolic acids and alkyl-substituted propiolic acids were
employed as coupling partners. The results are summarized in
Table 3. Electron donating group substituted-phenyl propiolic
acids such as 1b, 1c and 1d afforded the desired product 3p, 3c
and 3f with 67%, 77% and 69% yields, respectively (entries 1 –
3). Electron withdrawing group substituted-phenyl propiolic
acids also showed good yields (entries 4 and 5). Alkyl-substituted
propiolic acids such as hexynoic acid and pentynoic acid gave the
desired product 3p and 3q with 81% and 85% yields,
respectively (entries 6 and 7).
Ni
Ar
X
Ar
A
B
Ph
O
Ph
Base
+
CO2
HO
Scheme 1. Proposed mechanism.
Table 3. Ni-catalyzed decarboxylative coupling reactions between
aryl or alkyl propiolic acids and phenyl iodide.a
In summary, we have developed a synthesis of diaryl alkynes
involving the reaction of aryl iodides and phenyl propiolic acid in
the presence of a nickel catalyst. To obtain the desired product,
NiCl2 (10 mol%), Xantphos (15 mol%), Cs2CO3 (1.5 equiv), and
Mn (1.0 equiv) were employed. This method afforded diaryl
alkynes in moderate to good yields. Moreover, this methodology
presents several advantages over that used in traditional coupling
reactions of this sort: a stable Ni(II) source is employed as the
catalyst, and no formation of 1,4-diphenylbutadiyne, which is

4
Tetrahedron
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This research was supported by
a National Research
Foundation of Korea (NRF) grant provided by the Korean
government (MSIP) (NRF-2014R1A2A1A11050018, NRF-
2015R1A4A1041036) (S. Lee). The Ministry of Science and
Technology, Taiwan (MOST-105-2113-M-005-001) and the
National Chung Hsing University are also acknowledged for
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Highlights
Decarboxylative coupling reactions with alkynyl
carboxylic acid and aryliodides
Nickel-catalyzed decarboxyltive coupling
The employment of air stable nickel(II) as a
catalyst.

6
Tetrahedron
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Nickel-Catalyzed Decarboxylative Coupling
of an Alkynyl Carboxylic Acids with Aryl
Iodides
Yujeong Son, Han-Sung Kim, Ju-Hyeon Lee, Jisun Jang, Chin-Fa Lee*, Sunwoo Lee*
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