CuPd Nanoparticles as a Robust Catalyst for Electrochemical Allylic Alkylation

Article abstract of DOI:10.1002/anie.202006293

An efficient CuPd nanoparticle (NP) catalyst (3 nm CuPd NPs deposited on carbon support) is designed for catalyzing electrochemical allylic alkylation in water/isopropanol (1:1 v/v) and 0.2 m KHCO₃ solution at room temperature. The Pd catalysis was Pd/Cu composition-dependent, and CuPd NPs with a Pd/Cu ratio close to one are the most efficient catalyst for the selective cross-coupling of alkyl halides and allylic halides to form C?C hydrocarbons with product yields reaching up to 99 %. This NP-catalyzed electrochemical allylic alkylation expands the synthetic scope of cross-coupling reactions and can be further extended to other organic reaction systems for developing green chemistry electrosynthesis methods.

Full text of DOI:10.1002/anie.202006293

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Accepted Article
Title: CuPd Nanoparticles as a Robust Catalyst for Electrochemical
Allylic Alkylation
Authors: Zhouyang Yin, Huan Pang, Xuefeng Guo, Honghong Lin,
Michelle Muzzio, Mengqi Shen, Kecheng Wei, Chao Yu, Paul
Williard, and Shouheng Sun
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.202006293
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COMMUNICATION
CuPd Nanoparticles as a Robust Catalyst for Electrochemical
Allylic Alkylation
+
+
Zhouyang Yin, Huan Pang, Xuefeng Guo, Honghong Lin, Michelle Muzzio, Mengqi Shen, Kecheng
Wei, Chao Yu,* Paul Williard,* Shouheng Sun*
Abstract: We report an efficient CuPd nanoparticle (NP) catalyst (3 nm
selective allylic alkylation with product yields reaching as high as
99%. This CuPd NP-catalyzed electrochemical allylic alkylation
significantly expands the synthetic scope of cross-coupling
reactions heretofore impractical to common organic syntheses.[7]
CuPd NPs deposited on carbon support) for catalyzing electrochemical
3
allylic alkylation in water/isopropanol (v/v 1/1) and 0.2 M KHCO solution
at room temperature. The Pd-catalysis was Pd/Cu composition dependent
and CuPd NPs with Pd/Cu ratio close to 1 are the most efficient catalyst for
the selective cross-coupling of alkyl halides and allylic halides to form C-C
hydrocarbons with product yields reaching up to 99%. This NP-catalyzed
electrochemical allylic alkylation expands the synthetic scope of cross-
coupling reactions and can be further extended to other organic reaction
systems for developing green chemistry electro-synthesis methodologies.
The electrochemical synthesis was performed in air in a three-
electrode cell surrounded by a heating mantle that was used to
test reactions above room temperature (Figure 1a). A carbon rod
(
or Pt/Au gauze) was chosen as a counter electrode (CE).
Ag/AgCl immersed in water/isopropanol (v/v 1/1) solution of 2 M
KHCO (as a salt bridge) was used as a reference electrode
RE). Carbon paper (1 cm × 2 cm in dimension) loaded with NPs
3
(
Traditional chemical syntheses that generate large amount of
chemical wastes are under increased scrutiny due to the ever-
increasing demands on developing green chemistry processes
for chemical industries.[1] Electrochemical syntheses use
electricity to initiate redox reactions and have potentials in
promoting synthetic reactions under green chemistry
conditions.[ The mild electrochemical redox conditions also
make it possible to identify active intermediates for studying
reaction mechanisms.[3] Despite these promises, electrochemical
syntheses require the presence of catalysts, and these catalysts
are metal salts that are dissolved in the reaction solutions and
are difficult to separate/recycle. Furthermore, electrolytes and
solvents present in the reaction solutions are often toxic and
expensive[4] and not suitable as agents for green chemistry
reactions.
served as a working electrode (WE). To prepare the WE, 20 mg
of NPs deposited on 20 mg Ketjen carbon (Figure 1b&c, and
Support Information, SI) was mixed with polyvinylidene fluoride
(PVDF) and a few drops of N-methyl-2-pyrrolidone (NMP) and
the composite containing about 1 mg NPs was pasted on the
carbon paper, which was dried under vacuum at 35℃ overnight
to remove extra NMP. 20 mL water/isopropanol (v/v 1/1) solution
2]
3
of 0.2 M KHCO was used as the reaction solution.
Here, we report our studies using monodisperse CuPd
nanoparticles (NPs) as a robust heterogeneous catalyst for
cross-coupling of aliphatic halides to achieve allylic alkylation
under an environmental-friendly electrochemical condition.
Recently, metallic NPs have been studied extensively as
reusable catalysts in various electro-catalytic reactions, such as
oxygen reduction and CO
2
reduction reactions.[5] The synthetic
advances achieved in controlling NP size, composition, structure
and morphology have allowed the search of reaction hot spots
on the catalyst surface for further optimization of their catalytic
activity.[6] Studying Pd-based NPs as an electrocatalyst for
organic reactions, we found that they catalyzed the cross-
coupling of alkyl halide and allylic halide and realized the
selective allylic alkylation in water/isopropanol (v/v 1/1) at room
temperature with 0.2 M KHCO as the electrolyte. The Pd-
3
catalysis was Pd/Cu composition dependent and CuPd NPs with
Pd/Cu ratio about 1 were the most efficient catalyst for the
Figure 1. a) Schematic of an electrochemical cell containing three-electrodes
for electrochemical synthesis. b) Illustration of NP deposition on the carbon
support and their activation as
a
catalyst (working) electrode for
electrochemical synthesis. c) TEM image of CuPd NPs loaded on Ketjen
carbon prior to mixing with PVDF/NMP and deposition on carbon paper.
Previous studies on electrochemical allylic alkylation reactions
require the use of a zinc (Zn) anode to initiate the nucleophilic
reaction and Pd- and Cu-salts as catalytic components for the
reaction to produce higher yield C-C coupling products.[8]
However, under the reduction conditions, these Pd- and Cu-salts
tend to be reduced to metallic Pd and Cu, which makes it difficult
to identify the true catalytic sites. To prove that it is the metallic
species that catalyze the cross-coupling reaction, we prepared
[a]
Z. Yin, H. Pang, X. Guo, H. Lin, M. Muzzio, M. Shen, K. Wei, Y.
Chao, Prof. P. Williard, Prof. S. Sun,
Department of Chemistry, Brown University, Providence, Rhode
Island 02906
3
monodisperse 3 nm Pd NPs (Figure S1), Cu Pd NPs (Figure S2)
E-mail: chao_yu1@brown.edu
paul_williard@brown.edu
ssun@brown.edu
and CuPd alloy NPs (Figure S3) as new catalysts to study
Pd/Cu composition dependent catalysis for the cross-coupling
reaction in our electrochemical cell without using either Zn
electrode or Pd-/Cu-salts. The X-ray diffraction (XRD) (Figure
S4), high high-resolution TEM (HRTEM) and scanning
[+
]
These authors contributed equally to this work
Supporting information for this article can be found under:
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Angewandte Chemie International Edition
10.1002/anie.202006293
COMMUNICATION
transmission electron microscopy-electron energy loss
spectroscopy (STEM-EELS) (Figure S5) indicate that the as-
synthesized NPs have an fcc-type alloy structure. In the initial
reaction screening studies (Table 1), we found a mixture of
iodide with allylic chloride and obtained the cross-coupling
product in nearly quantitative yield (99%) (entry 4). These
observations imply that in the current CuPd-catalyzed reaction
condition, benzylic R
for the cross-coupling, and R
generating nucleophile to react with allylic compounds.
However, in the current reaction condition, R -X (X = Cl, Br)
1
-X (X = Br, I) activation is an important step
water and isopropanol (v/v 1/1) and 0.2 M KHCO
3
to be suitable
1
-I is more active than R -Br for
1
as the reaction solvent and electrolyte respectively (note that too
much water, for example water/isoproposal (v/v 3/1), led to poor
reaction outcome likely due to the poor solubility of the reactants
in the mixed solvent.). We first tested the cross-coupling product
yield over reaction time. The yield increased from 18% to 85% in
a 12 h reaction monitoring period (Figure S6). As shown in Table
a
1
bond in a 2-phenylethyl halide structure could not be activated to
react with allylic bromide, rather the structure underwent an
elimination process, forming an alkene (entries 5 and 6). When
X = I in the 2-phenylethyl halide structure, the cross-coupling
with allylic bromide could still dominate the reaction process
(85%) along with minor (5%) homo-coupling product (entry 7).
When 2-phenylethyl iodide reacted with allylic chloride, the
cross-coupling reaction was more selective (95%) (entry 8). Our
1
, at room temperature reaction conditions, CuPd NPs show
much higher activity (85%) than Pd NPs (66%), which comports
with the previous report that Cu plays important role for allylic
alkylation.[ However, too much Cu has a negative impact on
8a]
the Pd catalysis as Cu
3
Pd NPs show no activity for this reaction,
1
catalyst was even effective in activating R -I in 3-phenylpropyl
suggesting Pd is the dominant catalytic sites for C-X activation
and Cu acts as a co-factor and promotes the Pd-catalyzed
coupling reaction. A higher reaction temperature (50°C) or a
more negative reduction potential than -1.4 V tends to promote
homo-coupling of 2-phenylethyl iodide, which further implies that
in the reaction condition, 2-phenylethyl iodide is more easily
activated to serve as a nucleophile to react with allylic bromide.
The high yield formation of the coupling product also suggests
that the Zn electrode is not needed in the CuPd-catalyzed
coupling reaction. After each synthetic run, we washed the
catalyst (working) electrode with the fresh reaction solution and
re-used it to catalyze the cross-coupling reaction. In the 5th run,
the reaction still produced the coupling product at 80% yield
iodide (entry 9). These results show that an alkyl iodide can be
more easily activated on the CuPd catalyst surface to cross-
couple with allylic chloride to achieve the best yield for the cross-
coupling product.
Table 2 CuPd NP-catalyzed reactions of various alkyl halides (1) and allylic
halides (2) at room temperature.a
Product 4
(Yield %)
Product 5
(Yield %)
Entry
X
1
X
2
Product 3 (Yield %)
1
2
3
Br
Br
Br
Br
Br
Cl
-
-
-
-
-
-
(
90b)
(
Figure S7) and the morphology of the CuPd NPs did not
change (Figure S8), suggesting that the CuPd NP catalyst is
robust in its catalyzing the cross-coupling reaction.
(
95b)
(
(
95b)
Table
1 NP-catalyzed allylic alkylation in water/isopropanol (v/v 1/1) at
4
5
I
Cl
Br
I
Cl
Br
Br
Br
Cl
Cl
Cl
Cl
-
-
-
-
different reduction potentials at room temperature (R.T.) or at 50°C.
99b)
(99b)
(
(
0)
0)
6
b
(99 )
Catalyst
Potential
T(℃)
R.T.
R.T.
Time
Conversion
Yield(cross)
Yield(homo)
7
-
-
-
-
-
(
(
85c)
95c)
(93
(5b)
Pd NPs
-1.4 V
-1.4 V
12 h
12 h
86 %
90 %
66 %
85 %
20 %
5 %
8
I
-
CuPd NPs
Cu
3
Pd NPs
-1.4 V
-1.0 V
-1.6 V
-1.8 V
-1.4 V
R.T.
R.T.
R.T.
R.T.
50
12 h
12 h
12 h
12 h
3 h
N.R.
70 %
-
-
9
I
CuPd NPs
CuPd NPs
CuPd NPs
CuPd NPs
70 %
42 %
55 %
30 %
-
c
)
b
(
2 )
91 %
49 %
45 %
70 %
10
I
-
-
100 %
100 %
(43
b
)
1
1
1
2
I
(
50b)
I
Cl
-
-
(
94c)
Using the optimized reaction condition (-1.4 V vs Ag/AgCl,
R.T., 0.2 M KHCO and 1:1 water/isopropanol), we studied the
1
1
3
4
I
I
Cl
Cl
-
-
3
(35b)
(33b)
(
0)
scope of the allylation reaction (Table 2). For most cases, good
yields of the corresponding cross-coupling products were
obtained. The activated benzylic bromide reacted with allylic
bromide in 90% yield (entry 1). When a methyl group is present
at the ortho-position, a higher yield (95%) cross-coupling product
was separated (entry 2). To test the effect of different halide
groups on this allylation process, we replaced the allylic bromide
with allylic chloride and used it to react with benzylic bromide.
We saw a high yield (95%) synthesis of the corresponding
cross-coupling product (entry 3). We also reacted benzylic
(
0)
15
I
I
Br
Cl
(20
b
)
-
-
(
38b)
1
1
6
7
(92
b
)
-
I
I
I
Cl
Cl
Cl
-
-
-
(
0)
55b)
(
1
8
-
-
(
0)
19
(0)
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COMMUNICATION
a
Reactions were conducted on a 0.1 mmol scale for 12 h at room temperature
elimination reaction (44% yield) than Pd NP catalyst, and has
more preference to homo-coupling than to cross-coupling. The
selectivity of cross-coupling product on Pd NPs is high than that
on the Pd foil, and this selectivity is further improved by alloying
Pd with Cu. We also compared the reaction conversion yield of
in water/isopropanol (v/v 1/1) with 0.2 M KHCO
3
as the electrolyte. b GC yields
with n-tetradecane as an internal standard after acidification and aqueous
workup. c Isolated yields of products after column chromatography.
Next, we studied alkyl iodide reaction with the substituted
allylic halides (entries 10-14). With
observed cross-coupling products with moderate yields (entry 10,
3%, entry 11, 50%). It is noteworthy that with the ester
functional group as the R substituent, we achieved cross-
coupling product with high yield (entry 12, 94%). However, an
electron-donating R group hinders the cross-coupling reaction
and promotes, to some degree, homo-coupling reaction (entries
3 and 14), indicating that the allylation process in very sensitive
to the electronic character of R . Importantly and of considerable
2
a R substituent, we
different electrodes: carbon (C), C + Pd(acac)
CuPd/C in 12 h reaction time, as shown in Figure 2b. In the
presence of Pd(acac) , only 44% cross-coupling product was
observed probably because Pd(acac) needs to be reduced
before it shows the desired activity. The TEM image (Figure S9)
and ICP results (Figure S10) prove that some Pd(acac) and
Cu(acac) were reduced and grew into polydisperse NPs after
the reaction. As comparison, the pre-synthesized
2
, Pd/C and
4
2
3
2
4
2
2
1
a
4
monodisperse Pd NPs are much more active in promoting the
cross-coupling reaction, and this activity is further enhanced by
alloying Pd with Cu.
synthetic relevance, even long-chain alkyl halides can be cross-
coupled (entries 15 and 16) effectively with allylic chloride to
produce the cross-coupling product in 92% yield (entry 16). This
latter cross-coupling reaction expands the synthetic scope and
potential of our protocol and will be useful for achieving cross-
coupling reactions heretofore impractical under common organic
reaction conditions. It is worth noting that when we utilized allylic
bromide to react with this long-chain alkyl iodide, the yield of the
allylic bromide (20%) is significantly lower than the yield of the
allylic chloride (92%) because of a homo-coupling process (entry
The electronic binding properties of the Pd NP and CuPd NP
surfaces were studied by X-ray photoelectron spectroscopy
(
XPS). The XPS of Cu 2p (Figure 2c) show that Cu on the CuPd
NP surface has mixed valences of Cu/Cu(I) (932.3 and 952.0
eV) and Cu(II) (core peaks at 934.4 eV and 954.3 eV and
satellite peaks at 943.8 eV and 962.2 eV). The Pd 3d peaks (Pd
3
d5/2 and Pd 3d3/2) are at 336.3 eV and 341.5 eV for CuPd NPs,
1
5). Thus, the less reactive allyl chlorides afford higher yields
while the Pd 3d peaks of Pd NPs are at 335.7 eV and 341.0 eV
than allyl bromides (entries 7 and 8, entries 15 and 16),
indicating that an unusual reaction mechanism occurs in this
allylation process.
(
Figure 2d). Compared with the standard Pd 3d5/2 peak in 334.9
eV and Pd 3d3/2 peak in 340.1 eV for Pd foil,[9] the Pd 3d peaks
on both CuPd and Pd NPs shift to higher binding energy which
are close to Pd oxide peak (Pd2+ 3d5/2 336.4 eV, Pd2+ 3d3/2 341.6
eV).32 The shift of Pd 3d peak indicates that Pd is more
electropositive, which could facilitate its binding to
electronegative allylic compound via the double bond, and
therefore, nucleophilic substitution of the allylic halide bond. In
the reductive electrochemical reaction condition, the CuPd NP
surface can show the mixed valences of Cu/Cu(I)/Cu(II), which
Finally, to further test the ability of this reductive
electrochemical allylic alkylation, we reacted allylic chloride with
iodobenzene (entry 17), 4-iodoaniline (entry 18), and 4-
iodoanisole (entry 19). Although none of these reactions worked
in our system due to the occurrence of homo-coupling process
in entry 17 and the dehalogenation process in entries 17-19,
these results clearly build a precise substrate scope for this
alkylation reaction.
1
could contribute to its special catalysis ability in activating R -I
bond (via Cu(I)) and allylic-Cl bond (via Cu(II)) for their cross-
coupling.
In summary, we have demonstrated an efficient CuPd NP
catalyst for catalyzing electrochemical allylic alkylation in
water/isopropanol (v/v 1/1) and 0.2 M KHCO solution at room
3
temperature. Our new CuPd-catalyzed electro-allylic alkylation
differs from previous reports for similar alkylation reactions,
where Zn and metal salts are required to activate alkyl halides
for coupling with allylic halides, and our reaction occurs in
aqueous solution at room temperature. The alkyl halides,
especially alkyl iodides, show the highest activity and selectivity
towards their cross-coupling with allylic halides, especially allylic
chlorides when their double bonds are not deactivated by
electron donating groups. The cross-coupling catalysis on CuPd
NPs is likely enhanced by Pd-catalyzed alkyl halide activation
that is further promoted by the surface Cu binding to halides
(
probably via Cu(I)-I and Cu(II)-Cl bonding). In all, CuPd NPs are
Figure 2. a) Reaction product distribution of Pd foil, Pd NPs and CuPd NPs. b)
Cross-coupling product yield of Pd foil, Pd NPs and CuPd NPs after 12 h of
reaction at r.t. c) XPS of Cu 2p from CuPd NPs. d) XPS of Pd 3d from Pd NPs
and CuPd NPs.
a unique electro-catalyst that is active, selective and robust to
catalyze the cross-coupling of alkyl halides and allylic halides at
room temperature in aqueous solution. We are extending this
NP-catalyzed electrochemical reaction to other organic reaction
We compared the cross-coupling, homo-coupling and
elimination reaction product distribution of CuPd NPs, Pd NPs
and Pd foil (Figure 2a). Pd foil is more active to catalyze
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COMMUNICATION
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COMMUNICATION
COMMUNICATION
The CuPd nanoparticles could be
used as robust catalyst for
electrochemical reductive allylic
alkylation reaction in aqueous
solution.
Zhouyang Yin, Huang Pang, Xuefeng
Guo, Honghong Lin, Michelle Muzzio,
Mengqi Shen, Kecheng Wei, Chao Yu*,
Paul Williard* and Shouheng Sun*
Page No. – Page No.
CuPd Nanoparticles as a Robust
Catalyst for Electrochemical Allylic
Alkylation
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