Nickel/β-CD-catalyzed Suzuki–Miyaura cross-coupling of aryl boronic acids with aryl halides in water

Article abstract of DOI:10.1002/aoc.6378

In this study, a convenient nickel-catalyzed protocol has been introduced for the Suzuki–Miyaura coupling reaction. A simple mixture of Ni(II) and unfunctionalized β-cyclodextrin (β-CD) was used to cross-coupling of aryl halides with aryl boronic acids for the synthesis of biaryls in water. β-CD is a water-soluble seminatural cyclic oligosaccharide, environmentally friendly biomaterial, inexpensive, and commercially available ligand. This ligand with low solubility in usual organic solvents has been used for the synthesis of biaryls in good to excellent yields. The cross-coupling results in the presence of Ni(II)/β-CD catalytic system showed that the coupling reaction carried out with appropriate yields for both electron-rich and electron-deficient aryl halides. The coupling reaction completed in water as a green solvent. The catalyst was also recycled for four runs with a small decrease in its catalytic activity. The presented new method allows an easier and more cost-efficient synthesis of biaryls from the reaction of arylboronic acids with various aryl halides in water.

Full text of DOI:10.1002/aoc.6378

Received: 25 May 2021
DOI: 10.1002/aoc.6378
Revised: 23 June 2021
Accepted: 4 July 2021
R E S E A R C H A R T I C L E
Nickel/β-CD-catalyzed Suzuki–Miyaura cross-coupling of
aryl boronic acids with aryl halides in water
Sara Payamifar
| Foad Kazemi
| Babak Kaboudin
Department of Chemsitry, Institute for
Advanced Studies in Basic Sciences,
Zanjan, Iran
Abstract
In this study, a convenient nickel-catalyzed protocol has been introduced for
the Suzuki–Miyaura coupling reaction. A simple mixture of Ni(II) and
unfunctionalized β-cyclodextrin (β-CD) was used to cross-coupling of aryl
halides with aryl boronic acids for the synthesis of biaryls in water. β-CD is a
water-soluble seminatural cyclic oligosaccharide, environmentally friendly
biomaterial, inexpensive, and commercially available ligand. This ligand with
low solubility in usual organic solvents has been used for the synthesis of
biaryls in good to excellent yields. The cross-coupling results in the presence of
Ni(II)/β-CD catalytic system showed that the coupling reaction carried out
with appropriate yields for both electron-rich and electron-deficient aryl
halides. The coupling reaction completed in water as a green solvent. The
catalyst was also recycled for four runs with a small decrease in its catalytic
activity. The presented new method allows an easier and more cost-efficient
synthesis of biaryls from the reaction of arylboronic acids with various aryl
halides in water.
Correspondence
Babak Kaboudin, Department of
Chemsitry, Institute for Advanced Studies
in Basic Sciences, Gava Zang, Zanjan
45137-66731, Iran.
Email: kaboudin@iasbs.ac.ir
Funding information
Institute for Advanced Studies in Basic
Sciences
K E Y W O R D S
aryl boronic acids, biaryls, nickel, Suzuki–Miyaura coupling, β-Cyclodextrin
1 | INTRODUCTION
crystals, and conjugate polymers (Scheme 1).[14–19] The
costly palladium is the most routine catalyst for the vari-
The new bond formation is an important and applicable
process for the synthesis of valuable materials. The cross-
coupling reactions are efficient method for the carbon–
carbon bond generation that has developed by chemistry
scientists. The Suzuki–Miyaura coupling reaction is one
of the most utilized and general synthetic organic
transformation tools for the C(sp2)ÀC(sp2) bond forma-
tion.[1–13] The Suzuki–Miyaura coupling reaction is the
coupling between the organoboron reagents with organic
halides. The method is an extremely important and clean
protocol for the creation of different types of compounds,
especially biphenyls. Biaryl are versatile structural units
that have found many applications in natural products,
synthetic bioactive compounds, pharmaceuticals, liquid
ous cross-coupling reactions.[5,6,20] Due to high cost and
toxicity of palladium metal, the usage of the low-cost
transition metal complexes for the coupling reactions has
grown attention. In particular, nickel has been recog-
nized as a popular choice to replace with Pd for cross-
coupling reactions due to lower cost, high reactivity, and
earth-abundant.[21–23] Nickel catalysts in Suzuki–Miyaura
cross-coupling reactions commonly involve a combina-
tion of simple nickel salt with standard ligands such as
phosphines, N-heterocyclic carbenes, and pyridine
derivatives.[24–32] To date, many efforts have been made
for the development of Ni-based Suzuki reaction.
For instance, Lipshutz et al. reported nickel on charcoal
as an effective heterogeneous catalyst for the Suzuki
Appl Organomet Chem. 2021;e6378.
wileyonlinelibrary.com/journal/aoc
© 2021 John Wiley & Sons, Ltd.
1 of 8
https://doi.org/10.1002/aoc.6378

2 of 8
PAYAMIFAR ET AL.
reaction (Table 1). In order to optimize the reaction con-
ditions, the screening of various parameters such as sol-
vent, base, kind and amount of catalyst, and reaction
temperature were investigated, and the results are sum-
marized in Table 1. As indicated in Table 1, we examined
a set of experiments for optimizing the reaction condi-
tions. We have already reported the experimental data for
the screening of different copper salts on the coupling
reaction. In continuation, to find out the convenient cata-
lyst, three commercial Ni(II), Co(II), and Fe(III) salts
(5 mol%) were examined in the cross-coupling of 1a with
2a (1.2 equiv) in water as a solvent in the presence
K2CO3 (1.5 equiv) as a base at 65ꢀC under Ar. Results
showed that the reaction failed to give any desired prod-
uct 3a for 24 h. It was found that the reaction proceeded
with a mixture of transition metal salts (Ni, Co, and Fe)
with β-CD (5 mol%) (Entries 1–7). Screening of various
salts showed that the best result was obtained in the pres-
ence of Ni(II) sources, specially Ni(OAc)2. To get more
information on the optimal catalyst conditions, the reac-
tion was examined in different ratios of Ni(OAc)2 and
β-CD (Table 1). The reaction yield decreased to 49% when
the reaction was performed in 10 mol% β-CD (Entry 8).
Surprisingly, the compound 3a was obtained in 95% yield
in the presence of 2.5 mol% of β-CD (Entry 9). The reac-
tion proceeded smoothly to give compound 3a in only
13% yield with decreasing amount of Ni(OAc)2 to 2.5 mol
% (Entry 10). A decrease in yield was observed when the
reaction was carried out under air (Entry 11). The com-
pound 3a was obtained in 55% yield when the reaction
was performed at room temperature for 48 h (Entry 12).
Screening of various bases DABCO, Na2CO3, Et3N, and
NaHCO3 showed that the K2CO3 is the best (Entries 13–
16). The results in Table 1 showed that H2O was found as
a suitable solvent for the reaction while the reaction
yields decreased in other organic solvents (Entries 17–
20). Therefore, the best reaction conditions for the
employ of a mixture of Ni(OAc)2 and β-CD for the syn-
thesis of biaryl 3a contained the use of 5 and 2.5 mol% of
Ni(OAc)2 and β-CD, respectively, per mmol of 1a at 65ꢀC
in water for 24 h under Ar.
SCHEME 1 Examples of biaryl structure applications
reaction of functionalized aryl chlorides with boronic
acids.[33]
Recently, chemists have been more interested in the
use of water as an environmentally friendly, easily
available, and nonflammable solvent in organic synthe-
sis.[34–37] Reactions in aqueous media usually lead to high
selectivity, which cannot be obtained with organic
solvents.[38–42]
Cyclodextrins (CDs) are nontoxic materials that pre-
pared on large scale via the enzymatic degradation of
starch.[43,44] CDs have a hydrophobic inner cavity and a
hydrophilic outside with their ability to form inclusion
complexes with various kinds of molecules.[45–47] CDs
can be used as promoters or catalysts for various organic
reaction processes such as carbon–carbon bond forma-
tions, asymmetric synthesis oxidation, reduction, hydro-
lysis, and condensation.[48–54] Recently, functionalized
CDs have attracted attention for Suzuki–Miyaura cou-
pling reactions.[55–62] We have reported synthesis and
application of Cu(II)–β-CD complex in the homocoupling
reaction of aryl boronic acids.[63,64] Recently, we have
also reported Pd(II)–β-CD complex for the selective
Suzuki–Miyaura coupling reaction in water.[65] In contin-
uation of our interest for application of CDs in coupling
reactions, herein, we report a greener methodology for
the synthesis of biaryl compounds using a simple mixture
of Ni(II)/β-CD in water. In this report, we describe a
cross-coupling reaction of aryl halide compounds (X = I,
Br) with arylboronic acids in water in the presence of
catalytic amount of mixture of Ni(OAc)2 and β-CD.
Under the above optimized condition, the scope and
limitations of the mixed Ni(OAc)2/β-CD-catalyzed cross-
coupling reaction of various aryl halides with aryl
boronic acids were studied. The obtained results are sum-
marized in Table 2. The cross-coupling of phenyl boronic
acid with various aryl iodides having electron-rich and
electron-poor groups gave corresponding biaryls 3 in
good to excellent yields (Entries 1–6). The reaction of
4-iodotoluene with 1-naphthalene boronic acid,
2-benzofuranyl, and 3-thienyl boronic acid led to the
corresponding cross-coupling compound product with
good yields (Table 2, Entries 7–9).
2 | RESULTS AND DISCUSSION
Initially, the reaction of 4-iodotoluene (1a) with
phenylboronic acid (2a) was chosen as the model

PAYAMIFAR ET AL.
3 of 8
SCHEME 2 The coupling reaction of arylboronic acids
with aryl halides for the synthesis of biaryl 3
TABLE 1 Reaction of
4-iodotoluene 1a with phenylboronic
acid 2a in various reaction conditions
Entry
1
Catalyst
Solvent
H2O
Base
Reaction time (h)
Yield %a 3a
NiCl2.6H2O
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
DABCO
Et3N
24
24
24
24
24
24
24
24
24
24
24
48
48
48
48
48
48
48
48
48
41
2
Ni(NO3)2.6H2O
Ni(SO4)2.6H2O
CoCl2.6H2O
H2O
37
3
H2O
34
4
H2O
20
5
Co(OAc)2.6H2O
FeCl2.6H2O
H2O
22
6
H2O
29
7
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
Ni(OAc)2.4H2O
-
H2O
61
8
H2O
49b
95c
13d
63e
55f
53
9
H2O
10
11
12
13
14
15
16
17
18
19
20
H2O
H2O
H2O
H2O
H2O
trace
trace
85
H2O
NaHCO3
Na2CO3
K2CO3
K2CO3
K2CO3
K2CO3
H2O
DMSO
MeCN
EtOH
H2O
4
5
78
g
-
aGC yield (1-mmol 1a, 1.2-mmol 2a, 2-mmol base, metal salt [5 mol%], β-CD [5 mol%] in solvent [1 mL]
under Ar at 65ꢀC).
bThe reaction with 10 mol% of β-CD.
cThe reaction with 2.5 mol% of β-CD.
dThe reaction with 2.5 mol% of Ni (OAc)2.
eThe reaction carried out under air.
fThe reaction carried out at room temperature.
gThe reaction failed without any metal catalyst.
We have also examined the Suzuki reaction of aryl
showed that aryl bromides having electron-donating or
electron-withdrawing groups afforded biaryl compound
3 in good yields (Table 2, Entries 10–16).
The reusability of the mixture catalyst of Ni(OAc)2/
β-CD was also studied. The aqueous solution of the cata-
lyst was collected after washing the reaction mixture
with n-hexane. The catalytic activity did not decrease
considerably after four catalytic cycles (Table 3).
bromides. For this goal, the reaction of 4-bromoanisole
with phenylboronic acid was studied and the reaction
gave the compound 3i in 50% yield. However, when the
reaction temperature was increased to 85ꢀC, the reaction
yield was increased to 88%. Therefore, we studied the
coupling reaction of different aryl bromides with aryl
boronic acid at 85ꢀC in water. Generally, the results

4 of 8
PAYAMIFAR ET AL.
TABLE 2 The reaction of aryl halide 1 (1 mmol) with arylboronic acid (1.2 mmol) in the presence of Ni(OAc)2/β-CD catalyst
Entry
R
X
Ar
Product
Yield (%)a
1
p-Me
I
Ph
91
2
3
4
5
6
7
H
I
I
I
I
I
I
Ph
98b
p-MeO
p-Cl
p-NO2
p-F
Ph
90
Ph
85
Ph
90
Ph
89b
p-Me
1-naphthyl
82b
8
p-Me
p-Me
p-Me
I
2-benzofuranyl
3-thienyl
Ph
75b
87b
87c
9
I
10
Br

PAYAMIFAR ET AL.
5 of 8
TABLE 2 (Continued)
Entry
R
X
Ar
Product
Yield (%)a
11
H
Br
Ph
90c
88c
90c
90c
12
13
14
p-MeO
p-NO2
p-CHO
Br
Br
Br
Ph
Ph
Ph
15
16
p-CN
Br
Br
Ph
Ph
91c
90c
p-Acyl
aYields refer to isolated yields.
bGC yield.
cReaction carried out at 85ꢀC.
TABLE 3 Reusability test of the
Ni(OAc)2/β-CD catalyst in the reaction
of 4-iodotoluene 1a with phenylboronic
acid 2a in water
Product
3a
Yield (%) 1st run
95
2nd run
81
3rd run
4th run
Average yield (%)
78
74
82
Ni(II)/β-CD complex formation was examined by
ultraviolet–visible (UV–vis) spectroscopy. The absorbance
was recorded from 200 to 600 nm. The UV–vis absorption
spectra of Ni(OAc)2, β-CD, and complex of Ni(II)/β-CD
was shown in Figure S17. The results showed that the peak
at 273 nm in Ni(OAc)2 was disappeared in the Ni(II)/β-CD
complex spectrum. This is an evidence that Ni(II) has good
interaction with CD in Ni(II)/β-CD complex (Figure S18).
All efforts failed to prepare of appropriate crystal
samples of Ni(II)/β-CD complex for X-ray analysis.
On the basis of previous literature reports,[23,66,67] we
propose a plausible mechanism for the synthesis of biaryl
via the Ni(II)/β-CD-catalyzed coupling of aryl halides
with arylboronic acids (Scheme 3).

6 of 8
PAYAMIFAR ET AL.
Hertz (CDCl3 as solvent with reference chemical shifts of
1
δ = 7.26 for H NMR and δ = 77.0 for 13C NMR). Silica
gel column chromatography was carried out with
Silica gel 100 (Merck No. 10184). Merck Silica-gel
60 F254 plates (No. 5744) were used for the preparative
thin layer chromatography (TLC). Melting points are
uncorrected. Gas chromatography was performed on a
Varian CP-3800 chromatograph. UV–vis spectra were
recorded on a JASCO, UV-550 UV–vis spectrophotometer
(see Supporting Information UV–vis spectra of the
complex formation of a mixture of Ni(OAc)2.4H2O and
β-CD).
SCHEME 3 Proposed mechanism of coupling reaction of
arylboronic acids with aryl halides in the presence of Ni(II)/
β-cyclodextrin
3.2 | General procedure for the cross-
coupling aryl halides with aryl
boronic acids
At the first, Ni(0) species is generated in the presence
of β-CD. We assume that the role of β-CD is to stabilize
the active catalyst. The reaction may proceed via oxida-
tive addition of arylhalides to yield Ni(II) intermediate A.
In continuation, transmetalation of the aryl boronic acid
to intermediate A gives intermediate B. Finally, the
cross-coupled product is produced by a reductive elimina-
tion of intermediate B with regenerating the active
Ni(0) species.
In summary, herein, we reported a highly efficient
strategy Ni(II) catalyst for the Suzuki–Miyaura coupling
reaction of aryl halides with aryl boronic acids. The cata-
lyst was successfully applied for the coupling reaction of
a wide variety aryl halides (including electron-donating
and electron-withdrawing groups) with aryl boronic acids
in the presence of a mixture of Ni(OAc)2 (5 mol%)/β-CD
(2.5 mol%). The β-CD is a green, nontoxic, abundant,
inexpensive, and degradable natural product that can be
used as a ligand with Ni(OAc)2. This catalytic system is
environmentally green and cost-effective that could be
recycled and reused at least four times with a small loss
of catalytic activity. The presented process is a useful
method to present methodologies due to reusability of
the catalyst, use of water as a solvent, and clean
reactions.
In a 5-mL flask, Ni(OAc)2.4H2O (5 mol %) and β-CD
(2.5 mol %) were added to distilled water (1 mL), and
the mixture was stirred for 10 min. Aryl halide
(0.2 mmol), phenylboronic acid (0.24 mmol), and
K2CO3 (0.3 mmol) were added to the reaction mixture.
The mixture was stirred at 65ꢀC (aryl iodides) or 85ꢀC
(aryl bromides) for 24 h. The reaction mixture was
cooled to room temperature; the crude product was
extracted three times with n-hexane (3 Â 5 mL) and
dried over Na2SO4. The product was purified by
column chromatography with n-hexane–EtOAc (9:1) to
afford pure biaryl product 3 in good to high yields
(Table 2). All products were known and confirmed by
1H NMR and 13C NMR (see Supporting Information).
All products gave satisfactory spectral data in accord
with the assigned structures and literature reports
(Figures S1–S16).
ACKNOWLEDGMENT
The authors gratefully acknowledge support by the
Institute for Advanced Studies in Basic Sciences (IASBS)
Research Council.
AUTHOR CONTRIBUTIONS
Sara Payamifar: Investigation; methodology. Foad
Kazemi: Methodology. Babak Kaboudin: Investigation;
methodology; supervision.
3 | EXPERIMENTAL SECTION
3.1 | General
CONFLICT OF INTEREST
The authors declare no conflict of interest.
All chemicals were commercial products. Nuclear
magnetic resonance (NMR) spectra were obtained with a
400-MHz Bruker Avance instrument with the chemical
shifts being reported as δ ppm and couplings expressed in
DATA AVAILABILITY STATEMENT
Data availability statement: The data that supports the
findings of this study are available in the supplementary
material of this article.

PAYAMIFAR ET AL.
7 of 8
[34] P. A. Grieco, Organic Synthesis in Water, Springer Science &
Business Media 1997.
[35] C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media,
Wiley 1997.
[36] P. T. Anastas, J. C. Warner, Green Chem.: Theory Pract.
1998, 29.
[37] P. Tundo, P. Anastas, D. S. Black, J. Breen, T. Collins,
S. Memoli, J. Miyamoto, M. Polyakoff, W. Tumas, Pure Appl.
Chem. 2000, 72(7), 1207.
ORCID
Sara Payamifar https://orcid.org/0000-0002-8651-0102
Foad Kazemi https://orcid.org/0000-0001-8877-1173
Babak Kaboudin https://orcid.org/0000-0003-0495-0006
REFERENCES
[1] N. Miyaura, T. Yanagi, A. Suzuki, Synt. Commun. 1981,
11, 513.
[2] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
[3] F. Alonso, M. Yus, I. Beletskaya, Tetrahedron 2008, 64, 3047.
[4] A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722.
[5] C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot,
V. Snieckus, Angew. Chem. Int. Ed. 2012(51), 5062.
[6] H. Li, C. C. Johansson Seechurn, T. J. Colacot, ACS Catal.
2012(2), 1147.
[7] M. M. Heravi, E. Hashemi, Tetrahedron 2012, 68, 9145.
[8] F.-S. Han, Chem. Soc. Rev. 2013, 42, 5270.
[9] I. Maluenda, O. Navarro, Molecules 2015, 20, 7528.
[10] A. Chatterjee, T. R. Ward, Catal. Lett. 2016, 146, 820.
[11] A. Biffis, P. Centomo, A. del Zotto, M. Zecca, Chem. Rev. 2018,
118, 2249.
[12] P. Devendar, R.-Y. Qu, W.-M. Kang, B. He, G.-F. Yang,
J. Agric. Food Chem. 2018, 66, 8914.
[13] S. E. Hooshmand, B. Heidari, R. Sedghi, R. S. Varma, Green
Chem. 2019, 21, 381.
[14] G. Bringmann, R. Walter, R. Weirich, Angew. Chem. Int. Ed.
1990, 29, 977.
[15] R. Capdeville, E. Buchdunger, J. Zimmermann, A. Matter,
Nature Rev. Drug Disc. 2002, 1, 493.
[16] M. Kertesz, C. H. Choi, S. Yang, Chem. Rev. 2005, 105, 3448.
[17] J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651.
[18] F. S. Han, M. Higuchi, D. G. Kurth, Org. Lett. 2007, 9, 559.
[19] N. K. Adlington, L. R. Agnew, A. D. Campbell, R. J. Cox,
A. Dobson, C. F. Barrat, M. A. Gall, W. Hicks, G. P. Howell,
A. Jawor-Baczynska, J. Org. Chem. 2018, 84, 4735.
[20] I. P. Beletskaya, F. Alonso, V. Tyurin, Coord. Chem. Rev. 2019,
385, 137.
[21] S. Z. Tasker, E. A. Standley, T. F. Jamison, Nature 2014,
509, 299.
[22] V. P. Ananikov, ACS Catal. 2015, 5, 1964.
[23] J. B. Diccianni, T. Diao, Trends Chem. 2019, 1(9), 830.
[24] V. Percec, G. M. Golding, J. Smidrkal, O. Weichold, J. Org.
Chem. 2004, 69, 3447.
[25] B. M. Rosen, C. Huang, V. Percec, Org. Lett. 2008, 10, 2597.
[26] D. A. Wilson, C. J. Wilson, B. M. Rosen, V. Percec, Org. Lett.
2008, 10, 4879.
[27] Z.-Y. Tang, Q.-S. Hu, J. Org. Chem. 2006, 71, 2167.
[28] B.-T. Guan, Y. Wang, B.-J. Li, D.-G. Yu, Z.-J. Shi, J. Am. Chem.
Soc. 2008, 130, 14468.
[29] C. Chen, L.-M. Yang, Tetrahedron Lett. 2007, 48(13), 2427.
[30] X.-H. Fan, G. Li, L.-M. Yang, J. Organomet. Chem. 2011, 696,
2482.
[38] M.-O. Simon, C.-J. Li, Chem. Soc. Rev. 2012, 41(4), 1415.
[39] R. A. Sheldon, Chem. Soc. Rev. 2012, 41(4), 1437.
[40] T. Kitanosono, K. Masuda, P. Xu, S. Kobayashi, Chem. Rev.
2018, 118(2), 679.
[41] G. Cravotto, E. Borretto, M. Oliverio, A. Procopio, A. Penoni,
Cat. Com. 2015, 63, 2.
[42] R. N. Butler, A. G. Coyne, Org. Biomol. Chem. 2016, 14(42),
9945.
[43] J. Szejtli, Chem. Rev. 1998, 98(5), 1743.
[44] G. Crini, Chem. Rev. 2014, 114(21), 10940.
[45] A. R. Khan, P. Forgo, K. J. Stine, V. T. D'Souza, Chem. Rev.
1998, 98(5), 1977.
[46] G. Gattuso, S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998,
98(5), 1919.
[47] E. Engeldinger, D. Armspach, D. Matt, Chem. Rev. 2003,
103(11), 4147.
[48] S. V. Bhosale, S. V. Bhosale, Mini-Rev. Org. Chem. 2007,
4(3), 231.
[49] C. C. Bai, B. R. Tian, T. Zhao, Q. Huang, Z. Z. Wang, Molecules
2017, 22(9), 1475.
[50] L. Marinescu, M. Bols, Curr. Org. Chem. 2010, 14(13), 1380.
[51] K. R. Rao, Y. V. D. Nageswar, R. Sridhar, V. Reddy, Curr. Org.
Chem. 2010, 14(13), 1308.
[52] C. J. Easton, Pure Appl. Chem. 2005, 77(11), 1865.
[53] R. Breslow, S. D. Dong, Chem. Rev. 1998, 98(5), 1997.
[54] I. Tabushi, Acc. Chem. Res. 1982, 15(3), 66.
[55] M. Qi, P. Z. Tan, F. Xue, H. S. Malhi, Z.-X. Zhang, D. J.
Young, T. A. Hor, RSC Adv. 2015, 5(5), 3590.
[56] A. Cassez, A. Ponchel, F. Hapiot, E. Monflier, Org. Lett. 2006,
8(21), 4823.
[57] Y. Guo, J. Li, X. Shi, Y. Liu, K. Xie, Y. Liu, Y. Jiang, B. Yang,
R. Yang, Appl. Organomet. Chem. 2017, 31(4), e3592.
[58] F.-X. Legrand, M. Ménand, M. Sollogoub, S. Tilloy, E.
Monflier, New J. Chem. 2011, 35(10), 2061.
[59] V. V. Shinde, D. Jeong, S. Jung, Catalysts 2019, 9(2), 111.
[60] A. Z. Asadabadi, S. J. Hoseini, M. Bahrami, S. M.
Nabavizadeh, New J. Chem. 2019, 43(17), 6513.
[61] X. Zhao, X. Liu, M. Lu, Appl. Organomet. Chem. 2014,
28(8), 635.
[62] R. I. Khan, K. Pitchumani, Green Chem. 2016, 18(20), 5518.
[63] B. Kaboudin, Y. Abedi, T. Yokomatsu, Eur. J. Org. Chem. 2011,
2011(33), 6656.
[64] B. Kaboudin, R. Mostafalu, T. Yokomatsu, Green Chem. 2013,
15, 2266.
[31] Y. L. Zhao, Y. Li, S. M. Li, Y. G. Zhou, F. Y. Sun, L. X. Gao,
F. S. Han, Adv. Synth. Catal. 2011, 353, 2881.
[32] Y.-L. Zhao, G.-J. Wu, F.-S. Han, Chem. Commun. 2012, 48,
5868.
[65] B. Kaboudin, H. Salemi, R. Mostafalu, F. Kazemi, T.
Yokomatsu, J. Organomet. Chem. 2016, 818, 195.
[66] J. M. Bhojane, S. A. Sarode, J. M. Nagarkar, New J. Chem.
2016, 40, 1564.
[33] B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron
2000, 56, 2139.
[67] X. Lei, K. A. Obregon, J. Alla, Appl. Organomet. Chem. 2013,
27, 419.

8 of 8
PAYAMIFAR ET AL.
SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
How to cite this article: S. Payamifar, F. Kazemi,
B. Kaboudin, Appl Organomet Chem 2021, e6378.
https://doi.org/10.1002/aoc.6378