Pd-catalyzed cross-coupling reactions of arenediazonium salts with arylsilanes and aryltrifluoroborates in water

Article abstract of DOI:10.1016/j.tetlet.2013.09.001

Pd-catalyzed cross-coupling reactions of various arenediazonium salts with ArSi(OR)₃ and KArBF₃ have been achieved in good to excellent yields under simple aerobic conditions in water at room temperature. The functional group tolerance makes these transformations as attractive alternatives to the traditional cross-coupling approaches. Furthermore, the sequence can also be performed in a one-pot domino process, omitting the isolation of the intermediate arenediazonium salt.

Full text of DOI:10.1016/j.tetlet.2013.09.001

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Tetrahedron Letters 54 (2013) 6211–6214
Contents lists available at ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Pd-catalyzed cross-coupling reactions of arenediazonium salts
with arylsilanes and aryltrifluoroborates in water
Kai Cheng a, Baoli Zhao a, Sai Hu b, Xian-Man Zhang a, Chenze Qi a,
⇑
a Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, People’s Republic of China
b College of Materials Science and Chemical Engineering, Ningbo University, Ningbo 310014, People’s Republic of China
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 6 July 2013
Revised 20 August 2013
Accepted 2 September 2013
Available online 8 September 2013
Pd-catalyzed cross-coupling reactions of various arenediazonium salts with ArSi(OR)3 and KArBF3 have
been achieved in good to excellent yields under simple aerobic conditions in water at room temperature.
The functional group tolerance makes these transformations as attractive alternatives to the traditional
cross-coupling approaches. Furthermore, the sequence can also be performed in a one-pot domino pro-
cess, omitting the isolation of the intermediate arenediazonium salt.
Ó 2013 Elsevier Ltd. All rights reserved.
Keywords:
Palladium catalyzed cross-coupling
Arenediazonium salts
Environmental-friendly aqueous solution
One-pot domino process
Introduction
Moreover, the reactions can be often carried out at relatively low
temperatures because of much higher reactivities of the arene-
Green chemistry calls for the research development that can
improve the chemical syntheses in terms of resource efficiency,
environmental safety, energy efficiency, and operational simplic-
ity. One important aspect of such development is to perform the
desired chemical transformations in the environmentally friendly
aqueous solutions.1 In the past several decades, chemical transfor-
mations in the aqueous media have attracted tremendous atten-
tion for both academic researches and industrial productions.2
Most organic reactions are sluggish in the aqueous media
primarily due to the relatively low solubility of organic com-
pounds. Addition of phase-transfer catalysts3 or surfactants4 can
greatly enhance the solubility of the organic substrates in the
aqueous solutions. Indeed, this approach has been widely em-
ployed for numerous organic reactions performed in the aqueous
solutions to meet the demand for more environmentally benign
chemical transformations.
diazonium salts than the corresponding aryl halides as well as
the neutral nitrogen gas as the leaving group. Thus, additional
bases or additives are generally not required for the reactions of
arenediazonium salts. Furthermore, arenediazonium salts are rela-
tively insensitive to the electronic and steric effects of the adjacent
substituents, allowing the coupling reactions which are not appli-
cable to other methods. A variety of carbon–carbon chemical bond
formation reactions have been accomplished through the palla-
dium catalyzed coupling of arenediazonium salts.7 Few of these
palladium catalyzed coupling reactions are summarized in
Scheme 1, including aryl–aryl (Suzuki–Miyaura, Stille and Hiyama
crosscoupling, homocoupling),8 aryl–alkenyl (Mizoroki–Heck and
Hydroarylation),9 aryl–alkynyl (Sonogashira coupling),10 and car-
bonylation of aromatics.11
Palladium catalyzed-coupling reaction has been demonstrated
as one of the most powerful tools to construct the carbon–carbon
and carbon-heteroatom bonds in synthetic organic chemistry.5
For the palladium catalyzed coupling reactions, arenediazonium
salts clearly have the economical, environmental, and availability
advantages over the common electrophiles such as aromatic ha-
lides and triflates because they can be readily be synthesized from
the relatively inexpensive and widely available aromatic amines.6
Suzuki-Miyaura
Matsuda-Heck
R
Ar-Ar'
A
r
R
Ar'B(OH)2
Ar
H
Hydroarylation
Stille
Ar-Ar'
Ar-Ar'
R4Sn
R
R
R
R
Ar-N2BF4
Hiyama
Sonogashira
Ar
R
Ar'Si(OR)3
Homocoupling
R
H
Carbonylation
O
Ar-Ar
CO, NuH
Ar
Nu
⇑
Corresponding author.
E-mail address: qichenze@usx.edu.cn (C. Qi).
Scheme 1.
0040-4039/$ - see front matter Ó 2013 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.tetlet.2013.09.001

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K. Cheng et al. / Tetrahedron Letters 54 (2013) 6211–6214
Table 1
Hiyama
Suzuki-Miyaura
Pd-catalyzed Hiyama cross-coupling of arenediazonium tetrafluoroborate with
Ar-Ar'
arylsilanes in aqueous solutiona
Ar-N2BF4
Ar-Ar'
Ar'Si(OR)3
Ar'BF3K
in water
R2
TBAF
Pd(OAc)2
base
+ R1 Si R2
R2
R
N2 BF4
R
R1
TBAF
H2O, rt
Scheme 2.
Entry
R
R1
R2
Yieldb (%)
Although palladium catalyzed coupling reactions of arenediazo-
nium salts have become routine approaches in the synthetic organ-
ic chemistry, these transformations are generally performed in the
organic solvents. The transformation applied in environmentally
friendly aqueous solution is still limited. Furthermore, the Pd-cat-
alyzed cross-coupling in pure water is still difficult due to the poor
solubility of organic substrates.12 However, systematic research
about the homogeneous catalytic system for cross-coupling reac-
tions of the arenediazonium salts in pure water is necessary. In
the present Letter, we would like to present our recent results
about the efficient palladium catalyzed cross-coupling reactions
of arenediazonium salts with arylsilanes and aryltrifluoroborates
substrates (Scheme 2) in water at the ambient temperature with-
out the need of the inert-gas protection. The utility of our catalytic
system is further illustrated by the flexibility of being able to start
with an aniline substrate and employ an in situ diazonium forma-
tion process.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
C6H5
C6H5
4-OMe-C6H4
4-Cl-C6H4
4-Br-C6H4
4-NO2-C6H4
3-NO2-C6H4
2-Cl-C6H4
2,6-CH3-C6H4
1-Naphthyl
Phenanthren-9-yl
C6H5
C6H5
C6H5
4-Me-C6H4
3-F-C6H4
4-CF3-C6H4
Benzo[d]thiazol-2-yl
Benzo[d]oxazol-2-yl
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
OEt
83
82
80
84
80
73
81
78
73
80
82
65
70
74
69
70
66
OMe
OMec
OMe
OMe
OMe
OMe
OMe
OEt
OEt
OEt
OEt
OEt
OEt
OEt
OEt
OEt
a
Reaction conditions: arylsilanes (0.60 mmol), arenediazonium tetrafluoroborate
salts (0.50 mmol), Pd(OAc)2 (5.0 mol %), TBAF(75% w/w aq soln) (0.50 mmol) in
water (1.0 mL) at room temperature for 6 h.
Isolated coupling yields.
Using dimethoxydiphenylsilane instead of phenyltrimethoxysilane, the amount
of related arylsilanes was 0.30 mmol.
b
c
Results and discussion
Recently, we have reported that excellent yields could be
obtained from the palladium-catalyzed Hiyama cross-coupling
reactions of arenediazonium salts with organosilanes in alcoholic
solutions.8r But we did not observe any desired cross-coupling
products from the same reactions when repeated in aqueous solu-
tion. The low cross-coupling reactivities for these reactions could
be attributed to the insolubility of the organosilanes in aqueous
solutions, which was confirmed by the significant enhancement
of the cross-coupling reactivity by the addition of a phase transfer
reagent such as tetra-n-butylammonium fluoride (TBAF)
(Scheme 3).
A series of arylsiloxanes have been examined for the palladium
catalyzed cross-coupling reactions with different arenediazonium
tetrafluoroborate salts in aqueous solutions. Interestingly, all of
these reactions afford the related coupling products in moderate
to good yields as summarized in Table 1.
Examination of Table 1 shows that the alkyl groups of trialkoxy-
phenylsilanes seem to have negligible effects on the cross-coupling
reactions (Table 1, entries 1 and 2). Similarly, there are no observa-
ble effects on the cross-coupling of phenyltrimethoxysilane and
dimethoxydiphenylsilane with 4-methylbenzenediazonium salt
(Table 1, entries 2 and 3). Moreover, the electron-donating and
electron-withdrawing groups of the aromatic rings for both sub-
strates exhibit negligible effects on the coupling yields (Table 1).
Table 2
Palladium-catalyzed Suzuki–Miyaura cross-coupling of arenediazonium tetrafluoro-
borate salts with potassium aryltrifluoroborate salts in the aqueous solutiona
Pd(OAc)2
R1 BF3K
+
2 BF4
R
N
R R1
Na2CO3
H2O, rt
Entry
R
R1
Yieldb (%)
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
4-Me-C6H4
3-Me-C6H4
2-Me-C6H4
2,6-Me-C6H4
4-F-C6H4
4-Me-C6H4
4-Et-C6H4
4-t-Bu-C6H4
4-OMe-C6H4
3-OMe-C6H4
2-OMe-C6H4
4-Ac-C6H4
2-Naphthyl
85
81
77
70
65
61
78
73
67
69
82
83
76
68
79
74
71
73
quinolin-2-yl
pyridin-2-yl
H
H
H
H
H
H
H
H
3-F-C6H4
2-Cl-C6H4
4-MeO-C6H4
a
Reaction conditions: arenediazonium salts (0.5 mmol), potassium aryltrifluo-
roborate salts (0.6 mmol), Pd(OAc)2 (5.0 mol %), Na2CO3 (0.5 mmol), H2O (1 mL),
Pd(OAc)2
25 °C and 6 h.
+
H3C
N2 BF4
Si(OEt)3
H3C
b
room temp
CH3OH
Isolated cross-coupling yields.
81%
No product
Pd(OAc)2
+
+
H3C
H3C
N2 BF4
N2 BF4
Si(OEt)3
Si(OEt)3
room temp
H2O
These results clearly indicate that our palladium catalyzed system
is tolerant to the functional groups such as NO2, Cl, Br, and OMe
(Table 1, entries 9–12), which is difficult to be achieved by the
traditional Hiyama cross-coupling reactions, especially for bromide
(Table 1, entry 11). It is very interesting that some challenging
compounds with heterocyclic structures, such as 2-(trimethoxysi-
lyl)benzo[d]oxazole and 2-(trimethoxysilyl)benzo[d]thiazole, were
Pd(OAc)2
H3C
room temp
H2O
TBAF
83%
Scheme 3.

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K. Cheng et al. / Tetrahedron Letters 54 (2013) 6211–6214
6213
NaNO2, HCl
Pd(OAc)2, PhSi(OEt)3
H3C
NH2
H3C
without isolation
Scheme 4.
N2Cl
H3C
(76%)
-5oC, H2O
o
→
H2O,TBAF,-5 25 C
Catalyst Loading
NaNO2, HCl
-5oC, H2O
0.5 mol%: 39%
1 mol%: 44%
2 mol%: 52%
Pd(OAc)2, PhSi(OEt)3
H3C
NH2
H3C
o
→
H2O,TBAF,-5 25 C
0.1 mol
Scheme 5.
still capable of this transformation (Table 1, entries 7 and 8).
Furthermore, the steric effects seem to be also insignificant for
the palladium catalyzed cross-coupling (Table 1, entries 13–15).
To our delight, phenyl diazonium salts with PAH (Polycyclic Aro-
matic Hydrocarbon) could be coupled with PhSi(OEt)3 in moderate
yield (Table 1, entries 16 and 17).
intermediate arenediazonium chloride salt was generated in situ
and the subsequent cross-couping occurred without the isolation
of diazonium salt. The one-pot domino reaction from p-toluidine
via the Hiyama cross coupling resulted in the yield of 76%
(Scheme 4).
From a processing point of view, it is important to note that tra-
dition arenediazonium salts involved cross-coupling usually need-
ing high loads of catalysts in order to cross-couple efficiently. We
tested the one-pot domino process in large-scale with different
loadings of Pd(OAc)2. We are pleased to observe that even when
0.1 mol aniline was applied, moderate yield can be obtained for
these coupling reactions. 52% yield of biaryl was isolated in the
presence of 2 mol % catalyst. The system showed potential for
industrial application using arenediazonium salts with arylsilanes
via cross coupling (Scheme 5).
Many organoboron reagents have been developed as alterna-
tives to the boronic acids for the Suzuki–Miyaura (SM) cross-cou-
pling reactions.13 Potassium aryltrifluoroborates are the reagents
of choice for these transformations14 because of their relatively
simple preparation. For example, potassium aryltrifluoroborates
can be readily obtained from the treatment of the commercially
available arylboronic acids or esters in the aqueous KHF2 solution.
Most intriguingly, the aryltrifluoroborate salts are air-/moisture-
stable, in sharp contrast to the arylboronic acids.15 Moreover, aryl-
boronic acids are prone to form the cyclic or linear oligomeric
anhydrides, whereas aryltrifluoroborates are generally in the
monomeric state. Thus, aryltrifluoroborates will be more reliable
for any studies required for the accurate stoichiometric analysis.
The initial reaction of 4-CH3C6H4BF3K with benzenediazonium
salt in the aqueous solution was found to produce only 35% yield
of the cross-coupling product, in contrast to the 70–80% of the
cross-coupling yields for their corresponding arylboronic acids
even under the same reaction conditions. After careful examina-
tion of the cross-coupling reaction mechanism, we noticed that
hydrofluoric acid (HF) was formed as a by-product. Thus, we tested
different bases to neutralize the hydrofluoric acid by-product and
found that the cross-coupling yield could be significantly increased
by the addition of a suitable base. Na2CO3 was found as the most
efficient base among the tested bases to improve the cross-cou-
pling yields. For example, the cross-coupling product (4-methyl-
1,10-biphenyl) was isolated at a yield of 76% when Na2CO3 was
used as the base to neutralize the acid by-product. Most interest-
ingly, the optimized protocol also works well for the cross-cou-
pling reactions of other arenediazonium tetrafluoroborate salts
with aryltrifluoroborate salts (Table 2). This catalytic system seems
also to tolerate the functional groups such as –OCH3, –COCH3, –F,
and –Cl (Table 2, entries 4, 7, 13, and 15). No matter electron with-
drawing or electron donating substituents on the aromatic rings
they both coupling substrates exert negligible effects on the
cross-coupling yields. Notably, potassium quinolin-2-yl-trifluorob-
orate salt and potassium quinolin-2-yl-trifluoroborate salt can also
be used as efficient coupling partners for this reaction in moderate
yield (Table 2, entries 9 and 10).
Conclusion
In summary, we have demonstrated that arenediazonium salts
can be efficiently cross-coupled with different substrates including
ArSi(OR)3 and KArBF3 to afford the corresponding biaryls in good to
excellent yields under mild reaction conditions in aqueous solu-
tions. These transformations are tolerant to various functional
groups regardless of electron-donating or electron-withdrawing
groups. Otherwise, a one-pot cross-coupling process deriving from
anilines has been studied and the large-scale application with re-
duced loading of catalyst was also achieved. Further studies to en-
hance the catalytic activity of one-pot process and large-scale
appliance are currently under way in our laboratory.
Acknowledgments
This study was financially supported by the National Science
Foundation of China (Grant #21172149), the Science Technology
Department of Zhejiang Province (Grant #2012R10014-15) and
the Science Technology Project of Shaoxing (Grant.# 2013014017).
Supplementary data
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.tetlet.2013.09.
001.
References and notes
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apply our system to the cross-coupling sequence in a one-pot
domino process, extending the application of these reactions in
industry process. Firstly, we expertise the diazotizationin under
ꢀ5 °C, then we added palladium acetate and corresponding trieth-
oxy(phenyl)silane to the aqueous system, following this the reac-
tion temperature was raised to 25 °C. During this course, the
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