First Cp*Co(III)-catalyzed Mizoroki-Heck coupling reactions of alkenes and aryl bromide/iodide

Article abstract of DOI:10.1016/j.tetlet.2019.151283

A Cp*Co(CO)I₂ catalyzed Mizoroki-Heck coupling of alkenes and aryl halide is established at feasible reaction conditions. The Cp*Co(III) catalyst excellently work to couple the aryl iodide and alkene, and produce up to 94% yield of the coupling

Full text of DOI:10.1016/j.tetlet.2019.151283

Journal Pre-proofs
First Cp*Co(III)-Catalyzed Mizoroki-Heck Coupling Reactions of Alkenes and
Aryl bromide/Iodide
Avinash K. Srivastava, Naveen Satrawala, Munsaf Ali, Charu Sharma, Raj K.
Joshi
PII:
S0040-4039(19)31063-9
DOI:
https://doi.org/10.1016/j.tetlet.2019.151283
TETL 151283
Reference:
Tetrahedron Letters
To appear in:
Received Date:
Revised Date:
Accepted Date:
5 August 2019
9 October 2019
14 October 2019
Please cite this article as: Srivastava, A.K., Satrawala, N., Ali, M., Sharma, C., Joshi, R.K., First Cp*Co(III)-
Catalyzed Mizoroki-Heck Coupling Reactions of Alkenes and Aryl bromide/Iodide, Tetrahedron Letters (2019),
doi: https://doi.org/10.1016/j.tetlet.2019.151283
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First Cp*Co(III)-Catalyzed Mizoroki-Heck
Coupling Reactions of Alkenes and
Arylbromide/Iodide
Avinash K. Srivastava, Naveen Satrawala, Munsaf Ali,
Charu Sharma, Raj K. Joshi*

1
Tetrahedron Letters
journal homepage: www.elsevier.com
First Cp*Co(III)-Catalyzed Mizoroki-Heck Coupling Reactions of Alkenes and
Aryl bromide/Iodide
Avinash K. Srivastava, Naveen Satrawala, Munsaf Ali, Charu Sharma, Raj K. Joshi*
a
Department of Chemistry, Malaviya National Institute of Technology, Jaipur-302017, Rajasthan, INDIA
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A Cp*Co(CO)I2 catalyzed Mizoroki-Heck coupling of alkenes and aryl halide is established at
feasible reaction conditions. The Cp*Co(III) catalyst excellently work to couple the aryl iodide
and alkene, and produce up to 94% yield of the coupling product. In case of the coupling of aryl
bromide and alkene, slightly reduced activity of the catalyst was observed, and moderate to good
yield of the product was obtained. Apart from functionally different styrene, the catalyst was
also able to activate the acrylates, which seems difficult to be activated by other reported metal
complexes. The coupling proposed herein is tolerant a wide variety of aryl halides, stryenes, and
acrylates enable to form C-C bond using inexpensive metal in catalysis. Hence, the present
catalyst is highly economical, consists a non-endangered metal and is highly efficient for Heck
coupling reaction. Moreover, the cobalt metal in high oxidation state (+3) is not much explored
for the C-C cross-coupling reactions.
Available online
Keywords:
Mizoroki-Heck coupling
C-C bond formation
Co(III)
Metal carbonyl
2009 Elsevier Ltd. All rights reserved.
R
The Heck coupling is a profoundly noteworthy reaction
methodology for the formation of new C–C bonds, since, it is
one of the most common methods which allows coupling of
chlorides, bromides, and iodides with alkyl and aryl-substituted
olefins.1-2 This reaction has diversified applications which
includes the synthesis of biologically active molecules,3 natural
products,4-6 fine chemicals, active pharmaceutical ingredients
(APIs)7-9 and various novel polymeric materials.10 The catalysts
designed and widely used for Heck reaction mostly consist of N-
heterocyclic carbenes,11-15 phosphines16-17 and palladacycle18-19
systems. Heck reaction has significant applications in organic
and materials synthesis.20 However, even in present scenario most
of the reaction methodologies rely on palladium21-24 or nickel-
based catalytic systems.25 Significant drawbacks such as toxicity,
expensiveness, sensitivity for air and moisture of best known
catalysts restrict their application in scalable synthesis. Hence
there is a huge demand to address all these issues and replace the
noble metals with stable, economical and non-endangered metal
based complexes.
Fe2+ or Fe3+
X
+
R
Base, Ligand
100 - 130 C, 6 -24h
X = Br, I
R = Aryl, Acrylate
Benzyl
Scheme 1. Iron Catalyzed Heck Coupling Reactions
Apart from Fe metal, Ni complexes were also found to be
active for Heck coupling as shown in Scheme 2. In this context,
Inamoto and coworkers have reported an in situ complexation
and catalysis by Ni(acac)2 and NHC ligand.31,32 Further,
Ni(OAc)2 with PPh3 ligand is used by Zhao and coworkers.33
Norrby and coworkers have also reported Ni(COD)2 catalyst for
similar transformation reactions.34 Moreover, in 2009, Ni
nanoparticles were used as catalysts for the Heck coupling
reaction.35
R
Ni2+, Ligand
Base, >100C
16 -24h
X
+
R
In the last decade, various 3d transition metals have been
reported in the literature as potential catalysts for Heck reaction.
The Fe(II) and Fe(III) complexes26, 27 were identified as active
catalysts for the Heck reactions as shown in Scheme 1. In 2015,
Mankad and coworker used Na[FeCp(CO)2] complex as a
photocatalyst for Heck reaction.28 In 2017, Thomas and co-
workers reported the use of FeCl2 with Na2CO3 for Heck
coupling reaction.29 Hajipour and coworkers have also reported a
reusable FeCl3 based heterogeneous catalyst for the Heck
reaction.30
X = Br, I
R = Aryl, Acrylate
Scheme 2. Nickel-Catalyzed Heck Coupling Reactions
Recently, cobalt-catalyzed organic transformations have
attracted adequate attention, due to the easy availability,
environmental benignity, non-toxicity, inexpensiveness and
stability of the catalysts at room temperature. Thus, cobalt
complexes are one of the possible alternates to 4d and 5d
transition metals, which have the ability to fulfil the immediate
demand for coupling reactions (Scheme 3). In this context,
Oshima and coworkers have reported a CoCl2(DPPh) complex
with TMSCH2MgCl for Heck coupling.36 In 2007, Bao and
coworkers have reported Co nanoparticles for the similar reaction
under ligand-free conditions.37 Shao and coworkers used a flower
like Co nano structure in presence of K2CO3 for the Heck
reaction.38 Carriera and coworkers have reported a Co(III)

2
complex as a photocatalyst for similar transformations where the
reactions were performed under blue LED light source.39 Two
more reports, i.e. one in 2012 by Li and coworkers, and other in
2015 by Hajipour and coworkers, have used Co-B alloy and
multi-walled carbon nanotubes (MWCNT) supported Co-NHC
complex as a catalyst for Heck reactions.40,41
for sizeable transformations, whereas, yield was reduced when
mol% of the catalyst used was reduced (Table 1, Entry 17-19).
Table 1. Optimizations of various reaction parameters
Cat.
mol
%
Temp
(°C)
%
Entry
Catalyst
Base
Solvent
Yielda
R
X
1.
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
CoBr2
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
K2CO3
RT
50
20
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
ACN
NMP
Dioxane
Toluene
DMF
DMF
DMF
DMF
DMF
Trace
14
Co0 or Co2+ or Co3+
+
R
2.
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
15
10
5
Base, Ligand
>100C, 16 -24h
3.
80
35
X = Br, I
R = Aryl, Acrylate
Alkyl
4.
90
48
5.
100
120
120
65
Scheme 3. Cobalt Catalyzed Heck Coupling Reactions
6.
90
The metal carbonyls have high catalytic potential and several
organic transformations has been reported with various metal
carbonyls in recent past.42-47 Matsunaga and Kanai have reported
the Cp*Co(CO)I2 catalyst for C–H bond activation and gained
significant attention due to the unique selectivity and reactivity of
this carbonyl complex.48 To the best of our knowledge,
Cp*Co(CO)I2 complex is not yet explored for coupling reactions.
After having some preliminary success on the Cp*Co(III)
complex for Heck reaction, it is worthy to explore the detail
investigation. Herein, we report first Cp*Co(CO)I2 catalyzed
coupling reaction of styrene with aryl halides in the presence of
base K3PO4 and TBAB as oxidant (Scheme 4).
7.
68
8.
Na2CO3 120
64
9.
KOH
120
120
120
120
120
120
120
120
120
120
120
45
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
NaOH
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
K3PO4
42
50
65
46
42
Trace
12
CoCl2
R
X
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
Cp*Co(CO)I2
72
+
R
K3PO4, TBAB, DMF
120C, 24h
58
X = Br, I
22
R = Aryl, Acrylate
aIsolated Yields, Styrene (1.5 Equiv), Iodobenzene (1 Equiv)
Scheme 4. Cp*Co(CO)I2 catalyzed Heck coupling reaction
The yield of product with respect to time is presented in figure 1,
which shows an immediate increase in the yield of the product in
first 18h, which gradually approaches saturation in 24h.
However, no further improvement in the yield of product was
observed till 30h.
The selection of catalyst is a necessary prerequisite for the
catalysis. Relevant primary optimization indicates that
Cp*Co(III) complex works well for the Heck coupling of alkene
and aryl halides (Table 1). Various derivatives of aryl halides and
acrylates were examined in the presence of Cp*Co(CO)I2, base
(K3PO4) and oxidant TBAB. Almost nil conversion was
observed in the absence of base; hence, base is found to be an
essential requisite for the studied Heck coupling reaction. For the
base optimizations, various bases including Na2CO3, K3PO4,
K2CO3, NaOH, KOH were used (Table 1, entry 6-10), and K3PO4
was found to be the suitable base for the present transformation
reaction. However, Na2CO3 and K2CO3 also bring a satisfactory
yield in comparison to NaOH and KOH but did not match the
efficiency of K3PO4. Here, 2 equivalents of K3PO4 was found to
be highly suitable for optimum transformation. The amount of
base directly affects the rate of transformations as well as the
yield of the coupling product. By decreasing the amount of base
from 2 equivalents, corresponding decrease in the rate of reaction
as well as the yield of coupling product was observed. While
increasing the amount of base does not affect the reaction
productivity. Among several solvents ranging from non-polar
toluene, para-xylene to polar N, N-dimethylformamide (DMF),
N-methyl-2-pyrrolidone (NMP) and 1,4-Dioxane, DMF was
found to be highly suitable for the present reaction (Table 1,
Entry 11-14). The presence of TBAB was also found to be an
essential requisite for the faster and better conversion. Trace
Figure 1. Optimization of reaction time
After the optimized reaction condition, we embark the
substrate scope and found that the product yield strictly depends
on the type of halides used. Iodo-, bromo- and chloro- arylhalides
were used for the reaction. With iodobenzene, the reaction
produces exceptional results, while reactions with bromobenzene
produced low to average yield. Moreover, the catalyst was found
inactive to activate the chlorobenzene for the present Heck
reaction. Hence, Iodo- and bromo- benzenes were further
explored for Heck coupling with various styrenes (Table 2 and
3).
°
amount of product was obtained at 50 C, and by gradually
°
increasing the temperature up to 120 C, significantly increased
yield of the product was obtained (Table 1, Entry 2-6). Most of
the optimizations were performed at 120 °C temperature and the
catalyst Cp*Co(CO)I2 was found to be highly stable. The
performance of the catalyst at such a high temperature reflects its
robustness. Here 20 mol % of catalyst was found to be suitable

3
Table 2. Substrate scope for functionalized styrene with
bromobenzene
in 1:1.5 molar ratio. The aliphatic substrates i.e. ethyl acrylate
and n-butyl acrylate produced a sizeable yield of 82% and 84%,
respectively (Table 3, entry 7-8). The reaction of para-nitro and
para-methyl iodobenzene with styrene produced a substantial
yield of 76% and 80%, respectively (Table 3, entry 9-10). Further
reaction of para-nitro iodobenzene with para-methyl styrene
produced a significant yield of 78% (Table 3, entry11), while
with para-chloro styrene produced comparatively lower yield of
67% (Table 3, entry 12). A significant yield of 72% was
obtained for the reaction of para-methyl iodobenzene with para-
chlorostyrene (Table 3, Entry 13).
%
Entry
Alkene
Product
Yielda
1
52%
40%
2
3
32%
30%
Table 3. Substrate Scope for functionalized styrene with
iodobenzene
4
%
Entry
Alkene
Product
Yielda
5
6
1
90%
50%
28%
2
3
4
5
85%
80%
78%
75%
The reaction of Functionalised Aryl halides with Styrene
Entry
Halide
Product
%
Yielda
7
30%
8
9
32%
6
85%
Trace
7
8
82%
84%
aIsolated Yield, Catalyst (20 mol%), Solvent (DMF), Temp
(120 °C), Base (K3PO4), 24h.
It was observed that the presence of functional groups
influences the yield of corresponding product. The electron-
donating or withdrawing groups attached on either side (styrene
or bromobenzene) affects the product yield to a certain extent.
The reaction of bromobenzene with para-methyl styrene (Table
2, Entry 2) produces an average yield of 40%, the yield of
coupling product was further reduced when para-chloro- and
para-flouro styrene were used (Table 2, entry 3-4). Improved
yield of 50% of the coupling product was obtained with bulky
napthylstyrene (Table 2, entry 5). The aliphatic alkene, i.e. n-
butyl acrylate was also explored with bromobenzene, and the
average yield of 28% was observed (Table 2, entry 6). The
functionalized bromobenzene, i.e. the para-nitro and para-
methyl bromobenzene were also tested with styrene to widen the
substrate scope, and 30-32% yield of product was obtained
(Table 2, entry 7-8). Coupling of para-methyl chlorobenzene and
styrene was failed to give significant yield of product. However,
trace amount of the coupling product was obtained (Table 2,
Entry 9).
The reaction of Functionalised Iodobenzene with Styrene
%
Entry
Halide
Product
Yielda
9
76%
80%
78%
67%
72%
10
11
12
13
aIsolated Yield, Catalyst (20 mol%), Solvent (DMF), Temp
(120 °C), Base (K3PO4), 24h.
The reaction was further explored for different derivatives of
iodobenzene and various functionally substituted styrenes, and
outstanding yield of 90% of the corresponding coupling product
was obtained in the presence of Cp*Co(III) catalyst (Table 3,
entry 1). Using functionalized (para-methyl and -methoxy)
styrenes, a slightly reduced yield of 80-85% was obtained (Table
3, entry 2-3). Furthermore, a slightly reduced yield of 78% and
75% was obtained for para-chloro and -fluoro styrenes,
respectively (Table 3, entry 4-5). An excellent yield was recorded
with naphthyl styrene (Table 3, entry 6). Moreover, attractive
results were obtained when aryl halides and acrylates were taken
A plausible reaction mechanism for Cp*Co(CO)I2 catalyzed
Heck coupling reaction is proposed and depicted in Figure 2.
Here, the reaction is initiated, when the iodine of the complex
was abstracted by the base K3PO4 .49-51 This lead to the reduction
of Co(III) to (a) Co(I). Further, the activated Cobalt complex
undergoes an oxidative addition of halo benzene to form an
intermediate (b). Then, the intermediate (b) undergo insertion of
alkene via a concerted step to form an intermediate (c) and
subsequently gets converted into an intermediate (d). The
intermediate (d) reductively eliminated the desired product

4
alkene and converted to intermediate (e), which subsequently
looses the HBr and regenerates the active species in the reaction
for further coupling with alkene aryl halide.
9. Eisenstadt, A. Catalysis of Organic Reactions, ed. F. E.
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Figure 2. A plausible mechanism of Co(III) catalyzed Heck
coupling reaction
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Conclusion
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In conclusion, we have developed a facile method to convert
a wide range of styrene/acrylates and aryl halides to their
corresponding diphenylethene and cinnamates. These compounds
are obtained through a well known Mizoroki-Heck reaction
catalyzed by a high valent Cp*Co(III) carbonyl complex. The
complex is robust, inexpensive, highly efficient, easy to
synthesize, extremely stable under aerobic conditions and work
for wide range of functionalized alkene and aryl halides.
Moreover, this is the first report of Cp*Co(CO)I2 as a catalyst for
the Heck coupling reaction.
Acknowledgements
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R.K. Joshi thanks to DST (INT/RUS/RFBR/P0222) and CSIR
(01(2996)/19/EMR-II) for financial assistance. A. K Srivastava
thanks to MNIT Jaipur for research fellowship. Authors
acknowledge MRC, MNIT Jaipur for characterization facilities.
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Highlights
1. First report of Cp*Co(CO)I2 catalyzed
Mizoroki-Heck coupling reaction.
2. Catalyst works for wide range of
functionally substituted styrene/acrylates.
3. Arylbromide and aryliodide both found
active for the heck coupling reaction.
4. Methodology enables to achieve efficient
results via a cost effective catalysis.