Palladium-catalyzed carbonylative cross-coupling reaction of triarylantimony dicarboxylates with arylboronic acids: Synthesis of biaryl ketones

Article abstract of DOI:10.1016/j.jorganchem.2008.05.039

A novel palladium-catalyzed three-component carbonylative coupling reaction by use of triarylantimony diacetate, arylboronic acid and carbon monoxide (1 atm) could be attained under mild reaction conditions without any base as an additive. The reaction can be applied to a wide range of triarylantimony diacetates and boronic acids to afford the corresponding unsymmetrical biaryl ketones in good yields.

Full text of DOI:10.1016/j.jorganchem.2008.05.039

Journal of Organometallic Chemistry 693 (2008) 2949–2953
Contents lists available at ScienceDirect
Journal of Organometallic Chemistry
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Note
Palladium-catalyzed carbonylative cross-coupling reaction of triarylantimony
dicarboxylates with arylboronic acids: Synthesis of biaryl ketones
Weiwei Qin a,b, Shuji Yasuike a,b, Naoki Kakusawa a, Jyoji Kurita a,
*
a Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
b Organization for Frontier Research in Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 8 May 2008
Received in revised form 28 May 2008
Accepted 29 May 2008
Available online 4 June 2008
A novel palladium-catalyzed three-component carbonylative coupling reaction by use of triarylantimony
diacetate, arylboronic acid and carbon monoxide (1 atm) could be attained under mild reaction condi-
tions without any base as an additive. The reaction can be applied to a wide range of triarylantimony
diacetates and boronic acids to afford the corresponding unsymmetrical biaryl ketones in good yields.
Ó 2008 Elsevier B.V. All rights reserved.
Keywords:
Triarylantimony diacetate
Carbonylative cross-coupling
Palladium catalyst
Carbon monoxide (CO)
Arylboronic acid
Biaryl ketone
1. Introduction
oantimony compounds have been reported to date. For instance,
triarylantimony diacetates were successfully coupled under CO
Palladium(Pd)-catalyzed carbonylative coupling reaction of or-
ganic halides with various nucleophiles with main group elements
is an effective tool for the synthesis of a wide variety of symmetri-
cal and unsymmetrical ketones [1]. Among them, the reaction by
use of organoboron reagents such as arylboronic acids and arylbo-
ronates has attracted much interest on account of its high effi-
ciency, high chemoselectivity, and wide applicability [1,2].
However the development of the protocol by use of aryl halides
and arylboronic acids is limited due to a side reaction that gives
a direct coupling product without carbon monoxide (CO) insertion
[3]. In order to overcome this inefficiency, aryl diazonium salts [4]
and hypervalent iodines [5] were utilized as electrophiles instead
of aryl halides. It has also been reported that, in these reactions,
the nature of the substrate and electrophile as well as the reaction
conditions such as Pd catalyst, ligand, base, temperature, solvent
and pressure of CO brought about a dramatic effect on the selectiv-
ity in the formation of ketone and/or biaryl formed without CO
insertion.
atmosphere with alkynylsilanes [8] to form alkynyl ketones and
organostannanes [9] to give aryl- and vinyl ketones. We have also
recently demonstrated a new carbonylative cross-coupling reac-
tion between ethynylstibanes and aryl iodides to give ethynyl ke-
tones [10]. Meanwhile we have recently reported that
triarylantimony diacetates were useful coupling partners for Pd-
catalyzed cross-coupling reactions with a variety of arylboronic
acids and triarylbismuthanes, and the corresponding biaryls were
synthesized under mild reaction conditions without a base as a
activator of boron or bismuth reagent [11]. As an extension of this
work, we present here an efficient Pd(0)-catalyzed carbonylative
coupling reaction of triarylantimony diacetates as electrophile
with arylboronic acids under CO atmosphere to form symmetrical
and unsymmetrical diaryl ketones. It should be noted that the reac-
tion took place smoothly giving the expected coupling products
without any additive such as base for activation of boron or anti-
mony reagent.
Much attention has been paid to the chemistry of organoanti-
mony compounds which has widespread use for organic synthesis
[6,7]. However, to the best of our knowledge, only a few examples
of Pd-catalyzed carbonylative coupling reaction by use of organ-
2. Results and discussion
2.1. Optimization of the reaction conditions
In our previous work, we demonstrated the Pd-catalyzed
Suzuki-type cross-coupling reaction of pentavalent triarylantimony
diacetates with arylboronic acids, in that the reaction was performed
* Corresponding author. Tel.: +81 76 229 1165; fax: +81 76 229 2781.
E-mail address: j-kurita@hokuriku-u.ac.jp (J. Kurita).
0022-328X/$ - see front matter Ó 2008 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2008.05.039

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W. Qin et al. / Journal of Organometallic Chemistry 693 (2008) 2949–2953
in 1,4-dioxane at 60 °C in the presence of Pd(PPh3)4 catalyst
(5 mol%) without any base under argon atmosphere [11]. Else-
where it has been reported that the product distribution toward
the expected carbonylative cross-coupling product or direct
cross-coupling product without CO insertion was largely depen-
dent on the nature of solvents and additives [2,3]. Thus, we chose
the reaction of triphenylantimony diacetate (1a) with p-tolylbo-
ronic acid (2a, 3.0 equiv.) as a model system and searched for the
optimal reaction conditions for the expected carbonylative cross-
coupling reaction under CO atmosphere by using a variety of sol-
vents. The progress of the reaction was monitored by gas-liquid
chromatography (GLC) while measuring the yields of the coupling
product 3a and direct coupling product 4a, because 1a and 2a
could not be detected on thin-layer chromatography (TLC) or
GLC. The results are shown in Table 1. The reaction by use of 1,4-
dioxane, which has been shown to be the best solvent for direct
cross-coupling reaction between 1a and 2a to form 4a, gave unsat-
isfactory results in terms of the selectivity of the product. The reac-
tion afforded 3a in 75% yield accompanied by perceptible amounts
(24%) of direct coupling product 4a (Table 1, entry 1). When the
reaction was carried out in another ethereal solvent, tetrahydrofu-
ran (THF), the selectivity was considerably lowered and gave
approximately a 1:1 mixture of 3a and 4a (Table 1, entry 2). Similar
results were obtained by use of toluene and 1,2-dichloroethane
(1,2-DCE) and the expected improvement in the selectivity was
not observed (Table 1, entries 3, 4). In contrast, the use of polar
aprotic solvents such as dimethylacetamide (DMA) and N-methyl-
pyrrolidone (NMP) brought about desirable selectivity and car-
bonylated product 3a was formed in good yields with low yields
of uncarbonylated side product 4a, although acetonitrile gave
unexpected result in the yield of 3a (Table 1, entries 5–7). These re-
sults are in marked contrast to that, in the carbonylative coupling
reaction between aryl halides and boric acids, the use of ethereal
solvents such as dioxane led to the predominant formation of car-
bonylated coupling product in the best yield [3d]. The results in Ta-
ble 1 also show that one of three phenyl groups on the antimony
reagent can be coupled in the reaction. It is noteworthy that no
perceptible differences in the yield of 3a and the selectivity were
observed even when the amount of boronic acid 2a was reduced
from 3.0 equiv. to 1.5 equiv. (Table 1, entry 8). A perceptible
improvement in the yield of 3a was also observed when the pres-
sure of CO was increased from 1 (5%) to 20 atm (42%) at room tem-
perature in the present carbonylative cross-coupling reaction
(Table 1, entries 9–11). Consequently, the best result was obtained
when 1a was treated with 2a (1.5 equiv.) in the presence of
Pd(PPh3)4 (5 mol%) at 60 °C phenylboronic NMP as a solvent.
2.2. Carbonylative cross-coupling reaction of triphenylantimony
diacetate with arylboronic acids
In order to prove the generality of the present carbonylative
cross-coupling reaction, the reaction of triphenylantimony diace-
tate (1a) with various arylboronic acids (2b–i: 1.5 equiv.) was
examined in NMP under CO atmosphere (1 atm) by use of 5 mol%
Pd(PPh3)4. The reaction was carried out at 60 °C for 6 h and the re-
sults are summarized in Table 2. As a result, all boronic acids gave
the corresponding aryl ketones 3b–i in moderate to good yields. In
the case of 4-methoxyphenylboronic acid (2b), the reaction gave
carbonylated coupling product 3b in 83% yield accompanied by
15% yield of uncarbonylated coupling product, 4-methoxybiphenyl
(4b) (Table 2, entry 1). Similar results have been reported in the
carbonylative cross-coupling reaction between aryldiazonium tet-
rafluoroborate and electron-rich 2b, in that 23% yield of 4b was
formed as a side product along with 50% yield of carbonylated
coupling product 3b [4b]. We have also recently reported that
the direct cross-coupling reaction of 1a with electron-rich
4-methoxyphenyl- (2b) and 3,4-(methylenedioxy)phenylboronic
acid under argon atmosphere was completed in a shorter reaction
time than that of electron-deficient ones [11a]. These results imply
that the electron-rich boronic acids would promote transmetalla-
tion of the Pd-complex Ar2PdSbAr22 (OAc)2L2 (A) to Ar2PdAr1L2 (E)
shown in Scheme 1, and facilitate the pathway to give an uncarbony-
lated product without CO insertion. 1-Naphthylboronic acid (2c)
gave the desired product 3c in modest yield, which could be inter-
preted from unfavorable steric hindrance of the
a-naphthyl group
for the progress of the coupling reaction (Table 2, entry 2). In the
case of the boronic acids 2d–i bearing electron-withdrawing sub-
stituents, the reaction took place with high selectivity. Thus, the
reaction of 2d–i gave the corresponding biaryl ketones 3e–i in mod-
erate to good yields, and the formation of biaryls 4d–i was conspic-
Table 1
Carbonylative cross-coupling reaction of triphenylantimony diacetate 1a with 4-methylphenylboronic acid 2aa
H3C
B(OH)2
O
2a
Ph3Sb(OAc)2
H3C
+
H3C
Pd(PPh3)4 (5 mol%)
CO, 6 h
1a
4a
3a
Entry
Solvent
CO (atm)
Temperature (°C)
Yieldb (%)
3a
4a
1
2
3
4
5
6
1,4-Dioxane
THF
Toluene
1,2-DCE
CH3CN
DMA
NMP
NMP
NMP
1
1
1
1
1
1
1
1
1
60
60
60
60
60
60
60
60
rt
75
52
73
77
7
91
24
47
15
9
1
3
7
97 (95)c
97
5
2 (2)c
3
1
8d
9
10
11
NMP
NMP
5
20
rt
rt
38
42
1
1
a
1a (0.5 mmol), 2a (1.5 mmol), Pd(PPh3)4 (5 mol%), solvent (3 ml).
The yields of 3a and 4a were determined by GLC. The yield 100% corresponds to the involvement of one phenyl group on 1a.
Isolated yields.
2a (0.75 mmol).
b
c
d

W. Qin et al. / Journal of Organometallic Chemistry 693 (2008) 2949–2953
2951
Table 2
reaction, we finally attempted the reaction using a variety of triary-
lantimony diacetates having electron-donating 1b,c and -with-
drawing 1d–f groups with phenylboronic acid (2j) under the
same reaction conditions. The results are collected in Table 3.
When triarylantimony diacetates having 4-methoxy 1b, 4-methyl
1c, 4-chloro 1d, and 4-ethoxycarbonyl 1e substituents on the aryl
group were reacted under normal reaction conditions, the corre-
sponding carbonylative coupling products 3b, 3a, 3d, and 3j were
formed in good yields (81–95%) with high selectivity (Table 3, en-
tries 1–4). However, the antimony compound 1f owning electron-
withdrawing trifluoromethyl (CF3) group on position 4 of the ben-
zene ring gave the carbonylated product 3e in unsatisfactory yield
(60%) accompanied by a conspicuous amount of the uncarbonylat-
ed coupling product 4e: 18% (Table 3, entry 5). It has been reported
that, in the reaction of aryl halides with arylboric acids, the
Carbonylative cross-coupling reaction of triphenylantimony diacetate 1a with
arylboronic acids 2b–ia
1
O
Ar B(OH)
2
2b-i
1
1
Ph Sb(OAc)
3
2
Ar
Ar
+
Pd(PPh ) (5 mol%)
NMP, CO, 60 C , 6 h
3 4
1a
˚
4b-i
3b-i
Entry
Ar1 (2b–i)
Yieldb (%)
3
4
1
2
3
4
5
6
7
8
4-Methoxyphenyl (2b)
1-Naphthyl (2c)
4-Chlorophenyl (2d)
4-(Trifluoromethyl)phenyl (2e)
4-Acetylphenyl (2f)
4-(Methoxycarbonyl)phenyl (2g)
4-Cyanophenyl (2h)
3b: 83
3c: 52
3d: 92
3e: 81
3f: 83
3g: 64
3h: 91
3i: 81
4b: 15
4c: 7
4d: 1
4e: 4
4f: NDc
4g: 2
Table 3
Carbonylative cross-coupling reaction of triarylantimony diacetates 1b–f with
4h: 3
phenylboronic acid (2j)a
4-Nitrophenyl (2i)
4i: NDc
a
1a (0.5 mmol), 2b–i (0.75 mmol), Pd(PPh3)4 (5 mol%), NMP (3 ml).
Ph B(OH)
O
2
2j
2
b
Ar Sb(OAc)
3
Isolated yield. The yield 100% corresponds to the involvement of one phenyl
group on 1a.
2
2
2
+
Ar
Ar
3a, b, d, e, j
Pd(PPh ) (5 mol%)
3 4
c
Not detected.
1b-f
4a, b, d, e, j
˚
NMP, CO, 60 C, 6 h
uously suppressed (Table 2, entries 3–8). The results in Table 2 also
suggest that the electron-donating or -withdrawing substituents on
arylboronic acid do not affect the progress and the yield of 3 in the
present carbonylative cross-coupling reaction.
Entry
Ar2: 1b–f
Yieldb (%)
3
4
1
2
3
4
5
1b: 4-Methoxyphenyl
1c: 4-Methylphenyl
1d: 4-Chlorophenyl
1e: 4-Ethoxycarbonylphenyl
1f: 4-(Trifluoromethyl)phenyl
3b: 91
3a: 95
3d: 84
3j: 81
3e: 60
4b: 2
4a: 2
4d: 3
4j: 2
2.3. Carbonylative cross-coupling reaction of triarylantimony
diacetates with phenylboronic acid
4e: 18
a
1b–f (0.5 mmol), 2j (0.75 mmol), Pd(PPh3)4 (5 mol%), NMP (3 ml).
Isolated yield. The yield 100% corresponds to the involvement of one phenyl
b
In order to elucidate the correlation between reactivity and
electronic nature of the antimony reagent in the present coupling
group on 1.
PdL4
OAc
Ar2 Sb
Ar2
O
Ar2
Ar1
Ar2
1
OAc
3
PdL2
Oxidative
Reductive
elimination
addition
L
Ar1 B(OH)2
OAc
Ar2
Ar2
L
2
Ar2 Pd Sb
OAc
Ar2CO Pd Ar1
L
Transmetallation
L
D
A
Ar2 SbOAc
Ar2 SbOAc
2
2
+
+
CO
CO
AcOB(OH)2
AcOB(OH)2
L
Ar1
H
Ar2 Pd
L
O
O
HO
E
B
L
OAc
Ar2
Me
Ar1
Ar2CO Pd
O
Reductive
elimination
Ar2CO Pd Sb
Ar2
Ar2
Ar2
Sb
OAc
L
L
C
B
OAc
Transmetallation
Ar2 Ar1
4
Ar1 B(OH)2
2
Scheme 1. Proposed mechanism.

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W. Qin et al. / Journal of Organometallic Chemistry 693 (2008) 2949–2953
presence of a strong electron-withdrawing substituent such as ni-
tro group on the aryl halide inhibits CO insertion and promotes the
direct cross-coupling reaction [12].
coupling products in good yield, whereas electron-deficient anti-
mony reagent is relatively ineffective. The results show that the
use of an electron-poor boron reagent and an electron-rich anti-
mony reagent is preferable for the preparation of diaryl ketones
consisting of electron-rich and -poor aryl groups. This study re-
vealed the triarylantimony dicarboxylates to be practically useful
compounds as a synthetic reagent in organic synthesis.
2.4. Reaction mechanism
A plausible reaction mechanism of the present carbonylative
reaction is depicted in Scheme 1. It has been demonstrated in
our previous report that triarylantimony diacetate acts as a pseu-
do-halogen in the Pd(0)-catalyzed cross-coupling reaction with
boronic acids and triarylbismuthanes [11]. Taking these results
into consideration, the initial step of the present carbonylative
cross-coupling reaction is considered to be oxidative addition of
1 onto Pd(0) catalyst to form complex A [11,12]. The insertion of
CO between antimony–palladium bonds in complex A led to the
formation of complex B [3a,3c,12]. The formation of diaryl ketones
3 from the complex B should proceed along a similar pathway to
that of the direct cross-coupling reaction of 1 with 2 reported in
our previous paper [11]. Thus, transmetallation between the com-
plex B and boronic acid 2 gave diorganopalladium complex D via
intermediate C. In the intermediate C, the inter-coordination be-
tween boronic acid moiety and acetoxy group on antimony
(BÁ Á ÁO, OHÁ Á ÁO) would construct a six-membered ring to activate
boronic acid moiety and to accelerate the transmetallation in the
absence of a base. Indeed, boron reagents such as 5,5-dimethyl-
2-phenyl-1,3,2-dioxaborinane (2k), sodium tetraphenylborate
(2l), and potassium phenyltrifluoroborate (2m) having no ability
to form the six-membered ring were ineffective in the present
reaction. The carbonylated complex D thus formed undergoes
reductive elimination to give the carbonylative cross-coupling
product 3 and reproduces the Pd(0) species.
In the reaction with electron-poor triarylantimony diacetate 1f
bearing CF3 substituent on aryl group, a larger amount of the direct
cross-coupling product 4e was formed under the same reaction
conditions. This result can be explained as follows. It has been well
documented that the CO insertion into the transition-metal com-
plexes ArMXL2 (M = Ni, Pd, Pt) to form ArCOMXL2 was sensitive
to the electric nature of substituents on the aryl group; the inser-
tion was accelerated by the presence of an electron-donating sub-
stituent on the aryl group and was inhibited with an electron-
withdrawing one [13]. It has also been reported that, in the Pd-cat-
alyzed coupling reaction of p-substituted aroyl chlorides (ArCOCl)
4. Experimental
4.1. General
All reactions were carried out in pre-dried glassware under car-
bon monoxide (CO) atmosphere. Melting points were taken on a
Yanagimoto micro melting point hot-stage apparatus (MP-S3)
and are not corrected. 1H NMR (TMS: d 0.00 ppm as an internal
standard) spectra were recorded on
a JEOL JNM-ECA-400
(400 MHz) spectrometer in CDCl3 unless otherwise stated. Mass
spectra (EI-MS) were obtained on a JEOL JMS-700 instrument.
GLC analyses of the products were taken using a Shimadzu GC-
16A. All chromatographic separations were accomplished with Sil-
ica Gel 60N (Kanto Chemical Co., Inc.). Thin-layer chromatography
(TLC) was performed with Macherey-Nagel Pre-coated TLC plates
Sil G25 UV254. GLC analyses were performed by use of the follow-
ing conditions, 1.5% SE-30, 120–240 °C, 7.5 °C/min temperature
increasing program using n-octadecane [retention time
(tR) = 7.76 min] as an internal standard. High CO pressure reactions
were performed in a stainless steel reactor (100 ml) provided by
Taiatsu Techno Corp., Japan. NMP was purchased from Wako Pure
Chemical Ind. Ltd. Japan, and used without further purification. The
triarlyantimony diacetates 1 were prepared according to the re-
ported procedure [11b], and boron reagents 2 were purchased
from Wako Pure Chemical Industries, Ltd., Tokyo Kasei Kogyo Co.,
Ltd. Japan, Sigma-Aldrich, Inc. and Kanto Chemical Co., Inc.
4.2. Reaction of triarylantimony diacetates 1 with boron reagents 2
A mixture of triarylantimony diacetate 1 (0.5 mmol), boronic
acids 2 (0.75 mmol), and Pd(PPh3)4 (0.025 mmol) in NMP (3 ml)
was heated at 60 °C for 6 h under atmospheric pressure of CO. After
dilution with ether (40 ml) and water (20 ml), the reaction mixture
was separated and the aqueous layer was extracted with ether
(20 ml). The combined organic layer was washed with water, dried
over anhydrous MgSO4, and concentrated under reduced pressure.
The residue was purified by SiO2 column chromatography using a
mixture of hexane, dichloromethane, and ether as eluent to afford
biaryl ketones 3a–j and biaryls 4a–j, and the results are collected in
Tables 2 and 3. All products are known compounds and their struc-
tures were determined by comparing their melting points and/or
spectral data (MS and NMR) [15–20].
in the presence of distannane for the preparation of
a-diketones
[(ArCO)2], decarbonylated products (Ar2CO and Ar–Ar) were
formed as by-products, and the decarbonylation process was facil-
itated by electron-withdrawing substituents [14]. These results
imply that insertion of CO into the complex A to form the complex
B is in equilibrium with its reverse reaction from complex B to A
with decarbonylation, and the presence of an electron-withdraw-
ing substituent on the aryl ring not only retards the CO insertion
but also stimulates the decarbonylation. As a result, electron-with-
drawing CF3 substituent on the aryl group of 1f would promote the
formation of the direct coupling product 4e in the present reaction.
4-Methylphenyl phenyl ketone (3a): Colorless prisms, mp 54–
56 °C (lit. [15], 57–58 °C).
4-Methoxyphenyl phenyl ketone (3b): Colorless prisms, mp 61–
3. Conclusion
62 °C (lit. [15], 61–61.5 °C).
1-Benzoylnaphthalene (3c): Colorless prisms, mp 76–77 °C (lit.
[19a], 73 °C).
4-Chlorophenyl phenyl ketone (3d): Colorless prisms, mp 73–
75 °C (lit. [15], 73.5–75 °C).
4-Trifluoromethylphenyl phenyl ketone (3e): Colorless needles,
mp 116–117 °C (lit. [20], 112–114 °C).
4-Acetylphenyl phenyl ketone (3f): Colorless needles, mp 84–
85 °C (lit. [16], 80–84 °C).
4-Methoxycarbonylphenyl phenyl ketone (3g): Colorless plates,
mp 109–110 °C (lit. [17], 111–115 °C).
In summary, we have explored the Pd-catalyzed carbonylative
cross-coupling reaction of arylboronic acids using pentavalent tri-
arylantimony diacetates as an aryl donor and established a new
route to prepare asymmetrical diaryl ketones. The reaction pro-
ceeds smoothly in the presence of Pd(PPh3)4 as a catalyst in NMP
under mild reaction conditions without any base as additives in
that one of the three aryl groups on triarylantimony diacetate
can participate in the coupling reaction. Both electron-rich and
electron-deficient boronic acids gave the expected carbonylated

W. Qin et al. / Journal of Organometallic Chemistry 693 (2008) 2949–2953
2953
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4-Cyanophenyl phenyl ketone (3h): Colorless needles, mp 114–
116 °C (lit. [18], 113–114 °C).
4-Nitrophenyl phenyl ketone (3i): Pale yellow needles, mp
139.5–142 °C (lit. [15], 138–139 °C).
4-Ethoxycarbonylphenyl phenyl ketone (3j): Colorless prisms,
mp 48–49 °C (lit. [18], 54–55 °C).
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Acknowledgements
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574 (1999) 3;
This research was supported by a Grant-in-Aid for Scientific Re-
search (C) from the Ministry Education, Culture, Sports, Sciences
and Technology of Japan (to J. K); the ‘‘Academic Frontier” Project
for Private Universities from the Ministry Education, Culture,
Sports, Sciences and Technology of Japan (to S.Y and W.Q); and
the Sasakawa Scientific Research Grant from the Japan Science
Society (to W.Q). Financial support by The Specific Research Fund
of Hokuriku University is also gratefully acknowledged.
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