Microwave-Assisted Nickel-Catalyzed Rapid Reductive Coupling of Ethyl 3-iodopropionate to Adipic Acid

Article abstract of DOI:10.1007/s10562-020-03496-2

Abstract: 3-iodopropionic acid (3-IPA) can be efficiently synthesized from the glycerol derivative glyceric acid (GA), which is a potential biomaterial-based platform molecule. In this report, ethyl 3-iodopropionate was rapidly dimerized to diethyl adipate in a microwave reactor using NiCl₂·6H₂O as a catalyst, co-catalyzed by Mn and the 1, 10-Phenanthroline monohydrate ligand. Under the optimum reaction conditions, diethyl adipate can be obtained with 84% yield at 90?°C in just 5?min. Diethyl adipate was hydrolyzed to obtain the adipic acid (AA) in 89% yield with an acid catalyst. AA is an important chemical and a monomer for producing a wide range of high-performance polymeric substances. This rapid coupling method is also applicable to other alkyl halides. Graphic Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s10562-020-03496-2

Catalysis Letters
https://doi.org/10.1007/s10562-020-03496-2
Microwave‑Assisted Nickel‑Catalyzed Rapid Reductive Coupling
of Ethyl 3‑iodopropionate to Adipic Acid
Linfeng Zhang1,2 · Jing Zheng1,2 · Wenya Zou1,2 · Yongqi Shu1,2 · Weiran Yang1,2
Received: 20 October 2020 / Accepted: 11 December 2020
©
The Author(s), under exclusive licence to Springer Science+Business Media, LLC part of Springer Nature 2021
Abstract
3
-iodopropionic acid (3-IPA) can be efciently synthesized ꢀrom the glycerol derivative glyceric acid (GA), which is a
potential biomaterial-based platꢀorm molecule. In this report, ethyl 3-iodopropionate was rapidly dimerized to diethyl adi-
pate in a microwave reactor using NiCl ·6H O as a catalyst, co-catalyzed by Mn and the 1, 10-Phenanthroline monohydrate
2
2
ligand. Under the optimum reaction conditions, diethyl adipate can be obtained with 84% yield at 90 °C in just 5 min. Diethyl
adipate was hydrolyzed to obtain the adipic acid (AA) in 89% yield with an acid catalyst. AA is an important chemical
and a monomer ꢀor producing a wide range oꢀ high-perꢀormance polymeric substances. This rapid coupling method is also
applicable to other alkyl halides.
Graphic Abstract
Keywords Nickel catalyst · Wurtz coupling · Microwave-assisted · Adipic acid
Linꢀeng Zhang and Jing Zheng authors are contribute equally to
this work.
1
Introduction
Supplementary Information The online version contains
supplementary material available at https://doi.org/10.1007/s1056
As an important chemical, adipic acid can be used to pro-
duce nylon 6–6, polyurethanes, synthetic resins, thickeners,
and engineering plastics. It also plays an important role in
organic synthesis, medicine, lubricant manuꢀacturing, and it
can be directly used as ꢀood additives and ꢁavoring agents,
etc. [1–6]. Its output ranks second among all dicarboxylic
acids, and it still maintains an annual growth rate oꢀ 3%
[7–9].
2
-020-03496-2.
*
Weiran Yang
wyang16@ncu.edu.cn
1
School oꢀ Resources Environmental and Chemical
Engineering, Nanchang University, Nanchang 330031,
Jiangxi, China
2
Key Laboratory oꢀ Poyang Lake Environment and Resource
Utilization, Nanchang University, Nanchang 330031, Jiangxi,
China
Vol.:(0
1
123456789)
3

L. Zhang et al.
At present, the production oꢀ adipic acid mainly relies on
petroleum. The traditional method is to hydrogenate benzene
to obtain cyclohexane, which is then oxidized to a mixture
oꢀ cyclohexanol and cyclohexanone (KA oil), and oxida-
tion oꢀ KA oil by concentrated nitric acid provides adipic
acid (AA) [10, 11]. Companies such as BASF oꢀ Germany
and DuPont oꢀ the USA have successꢀully developed a new
process to produce AA ꢀrom butadiene. For example, BASF
uses pyridine as a promoter and Co (Co) as a catalyst in the
Previous work:
Na/Mg/Ni(CO)
/t-BuLi
4
(R = alkyls or aryls) (a)
RX
R-R
F3Si-Ph
Ph-R
Cl Sn-Ph
3
PhR
PhR
Ni/Ligands
RX
(R = alkyls)
(b)
(
HO) B-Ph
2
2
8
reaction where the butadiene (ꢀrom the cracked petroleum
component) reacts with carbon monoxide and methanol
under high temperature and high pressure to produce dime-
thyl adipate in two steps [12]. Then a lot oꢀ water and acidic
ion exchange resin were used to get puriꢂed adipic acid with
up to 72% yield. With the depletion oꢀ the non-renewable
R-ZnBr
R-R
R-R
Ir, Cu, Fe, Pd
RX
(R = alkyls or aryls) (c)
This work:
Ni/Ligand
(
d)
ꢀ
ossil ꢀuel resources and concerns about the environmental
R-R
(R = alkyls)
RX
Microwave-assisted
problems during its usage, the use oꢀ sustainable biomass
resources to produce adipic acid is the research area oꢀ cur-
rent interest. For example, Wang and co-workers reported
that ReO /ZrO efciently catalysed the deoxydehydration
Scheme 2 Previous synthesis oꢀ bialkyls via alkylhalide coupling
x
2
oꢀ D-glucaric acid-1,4-lactone, oꢃering adipic acid ester
with two steps in 82% yield [2]. In 2019, Wang also demon-
strated the synthesis oꢀ adipic acid ꢀrom 2,5-ꢀurandicarbox-
ylic acid, originated ꢀrom cellulose-based 5-hydroxymethyl-
it has limitations ꢀor the reaction oꢀ secondary alkyl hal-
ides. Transition metal-catalyzed cross-coupling oꢀ halo-
gen compounds to ꢀorm carbon–carbon bond is among the
most powerꢀul methods in organic synthesis [28, 29]. Fu
etc. reported the efcient coupling oꢀ unactivated primary
and secondary alkyl halides with alkylzincs, arylboronic
acids monoorganotin or organosilicon reagents together in
the presence oꢀ ligands and nickel catalysts (Scheme 2b)
[30–33]. Recently, methods mediated by stoichiometric (Ir
or Cu) or catalytic (Pd, Fe, or Cu) amount oꢀ metals have
been developed (Scheme 2c) [34–38], but their scope and
ꢀunctional-group compatibility is limited. Another method
oꢀ reductive coupling oꢀ alkyl halides is to convert part oꢀ
alkyl halides into organometallic reagents, and then react
with the remaining alkyl halides [39]. However, their appli-
cation in dimer molecular synthesis has some disadvantages,
including sensitive to air and water, an oꢀten narrow sub-
strate scope and a low reaction rate [40–42]. Thereꢀore, the
development oꢀ an efcient method ꢀor the generation oꢀ
bialkyls via alkylhalide coupling, particularly in mild con-
ditions, is oꢀ great importance in organic synthesis and ꢀor
practical applications.
ꢀ
[
urꢀural, using a platinum catalyst under hydrogen in water
13]. Recently, Tomishige and co-workers reported that the
2
-methoxycyclohexanone (2-MCO) can be selectively con-
verted to adipic acid catalyzed by H PW O [14].
3
12 40
With the expansion oꢀ the biodiesel market, the supply oꢀ
its by-product glycerol has exceeded its demand [15]. Glyc-
erol has been converted to a variety oꢀ value-added prod-
ucts, such as glyceric acid [16–19], 1,2-propandiol [20–22],
1
,3-propandiol [23–25]. In our previous work, we developed
a method to convert glyceric acid to 3-iodopropionic acid
3-IPA) with up to 99.9% yield under the catalysis oꢀ hydroi-
(
odic acid [26]. 3-IPA is an important platꢀorm chemical that
can be converted to various value-added products due to
the reactivity oꢀ the halide group. The present work mainly
explores the technology oꢀ producing adipic acid through
3
-IPA coupling, aiming to establish the process oꢀ adipic
acid production ꢀrom glycerol (Scheme 1).
Alkylhalides coupling to ꢀorm bialkyls in mild con-
dition is oꢀ great interest. The classical method is Wurtz
coupling mediated by sodium metal (Scheme 2a) [27].
However, the use oꢀ the reactive Na metal is a concern and
3
3
Here we ꢀurther improved the Csp –Csp bond ꢀormation
method [39, 43–45] by using microwave-assisted heating ꢀor
O
Vegetable oil
Animal fat
OH
OH
Hydrolysis
O
2
Rh/C
HI
I
OH
OH
HO
OH
HO
OH
HO
O
O
O
Scheme 1 Proposed reaction path ꢀrom glycerol to adipic acid
1
3

Microwave-Assisted Nickel-Catalyzed Rapid Reductive Coupling of Ethyl 3-iodopropionate…
the synthesis oꢀ bialkyls ꢀrom alkylhalides (Scheme 2d). The
potential oꢀ microwave-assisted heating has been well explored
in organic synthesis as a non-classical approach to enhance
yields in signiꢂcantly short reaction time [46–48]. To the best
oꢀ our knowledge, alkyl halides coupling catalyzed by nickel
solvent ꢀor 24 h [50]. The yield oꢀ adipic acid (AA) was
only 9% (Table 1, entry 1). The yield oꢀ the product did not
improve much when increasing the temperature to 90 °C
(Table 1, entry 2). We speculated that the carboxyl group
may hinder the reaction, so ethyl 3-iodopropionate was then
used as the substrate. Fortunately, the product (diethyl adi-
pate) yield increased to 45% at 40 °C (Table 1, entry 3).
Neither raising the temperature nor prolonging the reaction
time could ꢀurther improve the yield dramatically, and the
side product was ethyl propionate probably by direct reduc-
tion (Fig. S1) (Table 1, entries 4–5). The structure oꢀ the
coupling product diethyl adipate was characterized and con-
3
3
compounds with microwave irradiation via Csp –Csp cross-
coupling has not been described yet in literature. Herein, by
using microwave irradiation and nickel-based catalysts, 84%
yield oꢀ diethyl adipate can be obtained in 5 min ꢀrom ethyl
3
-iodopropanoate. And the ꢀunctional group tolerance with
this method is conꢂrmed to be good. The reaction mechanism
was also deduced based on Weix’s proposal [49] and some
control experiments.
1
ꢂrmed via H NMR analysis as well as high-resolution mass
spectrometry (HRMS) as shown in the supporting inꢀorma-
tion (Figs. S2 and S3).
2
Experimental Section
To ꢀurther improve the reaction efciency, microwave
radiation was used to ꢀacilitate the reaction. First, the opti-
mal reaction temperature and reaction time were explored,
and it was ꢀound that 90 °C and 5 min could provide the
best result (see supporting inꢀormation in Table S1).
With the same reaction reagents as in Table 1, entry 5,
78% yield oꢀ the product can be obtained in 5 min under
microwave radiation, which is a big advancement com-
pared to the traditional method. Then, several diꢃerent
nickel-based catalysts [30, 32, 33] were tested (Table 2,
entries 1–5). It was ꢀound that NiCl ·6H O provided the
2
.1 Materials
All chemicals and materials, ethyl 3-iodopropionate (98%,
Aladdin), Mn (> 98%, Aladdin), NiCl ·6H O (98%, Inno-
2
2
chem), 1, 10-phenanthroline monohydrate (≥99.0%, Inno-
chem), H SO (≥98%, Xilong Scientiꢂc), DMSO (≥ 98%,
2
4
Xilong Scientiꢂc), CDCl (99.9%, Innochem) and n-dode-
3
cane (≥99.0%, Aladdin), were commercially available and
directly used without ꢀurther treatment.
2
2
2.2 Catalytic Reaction and Product Analysis
best result. Besides, NiCl ·6H O is the cheapest among
2 2
all the Ni catalyst tested. Next, several diꢃerent ligands
(b-d) were screened. The replacement oꢀ 1, 10-phenanth-
roline monohydrate (a) with other ligands (b-d) did not
increase the yield (Table 2, entries 6–8). And, the yield
was ꢀound to be very low without any ligand (Table 2,
A ꢁame-dried 10 mL Schlenk tube equipped with a mag-
netic stirring bar was charged with NiCl ·6H O (2.38 mg,
2
2
0
.01 mmol), 1, 10-phenanthroline monohydrate (a)
(
1.98 mg, 0.01 mmol) and Mn (55 mg, 1 mmol). N was
2
used to displace the air, ꢀollowed by the addition oꢀ substrate
ethyl 3-iodopropionate (1 mmol) and DMSO (2 mL). The
reaction mixture was stirred in a microwave reactor (100 W)
at 90 °C ꢀor 5 min. The cooled and ꢂltered product was
tested by GC/MS (Agilent 6890-5973 N) and GC (Agilent
Table 1 Eꢃect oꢀ temperature and reaction time on the reaction
6
890 N, HP-plot Q capillary column FI detector).
1
H NMR (Bruker Ascend 400 M) spectra were recorded
at 400 MHz NMR spectrometer using CDCl as solvent,
3
Diethyl adipate and ꢀree radicals were detected by LC–MS
Reaction Conv. (%) Yield (%)a
time(H)
(
SCIEX, UPLC-X500RQTOF). Aꢀter the reaction, a cer-
Entry
T (°C)
(
Oil
tain amount oꢀ n-dodecane was added to the product as the
internal standard, which was detected in GC. The conversion
rate and yield were calculated based on the peak area ratio
oꢀ n-dodecane and diethyl adipate.
bath)
1 (R=H)
2 (R=H)
40
90
40
90
90
24
24
24
24
36
40
46
>99
>99
>99
9
10
45
53
54
3
4
(R=Et)
(R=Et)
3
Results and Discussions
5 (R=Et)
All the reactions were perꢀormed on a 1 mmol scale
Yields were determined by GC with n-dodecane as an internal standard
First, we attempted to dimerize 3-IPA using NiCl (glyme)
2
a
catalyst, and 1,10-phenanthroline monohydrate as the ligand,
together with 1 equivalent oꢀ Mn powder at 40 °C in DMSO
1
3

L. Zhang et al.
Table 2 Screening oꢀ optimal reaction conditions
Entry
Catalyst
Ligand
Solvent
Reducing agent (eq)
Conv. (%)
Yield (%)a
1
2
3
4
5
6
7
8
9
NiCl (glyme)
a
a
a
a
a
b
c
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMF
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (1)
Mn (2)
Mn (0.5)
Fe (1)
>99
>99
24
78
75
19
13
84
68
57
49
20
71
52
69
86
71
N.D
11
82
79
2
NiBr (glyme)
2
NiO
Ni(Ac) ·4H O
40
2
2
NiCl ·6H O
>99
>99
88
83
66
>99
91
>99
>99
87
12
23
2
2
NiCl ·6H O
2
2
NiCl ·6H O
2
2
NiCl ·6H O
d
-
2
2
NiCl ·6H O
2
2
1
1
1
1
1
1
1
1
1
0
1
2
3
4
5
6
7
8
NiCl ·6H O
a
a
a
a
a
a
a
a
a
2
2
NiCl ·6H O
DMI
2
2
NiCl ·6H O
DMAC
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
2
2
NiCl ·6H O
2
2
NiCl ·6H O
2
2
NiCl ·6H O
2
2
NiCl ·6H O
Zn (1)
Mn (1)
Mn (1)
2
2
b
c
NiCl ·6H O
>99
>99
2
2
NiCl ·6H O
2
2
All the reactions were perꢀormed on a 1 mmol scale with microwave irradiation in 5 min
a
Yields were tested by GC with n-dodecane as an internal standard
Added an equivalent NaI
ethyl 3-iodopropionate 1.04 g (4.56 mmol)
b
c
entry 9). Diꢃerent solvents were also studied ꢀor a better
result. Solvent has a big eꢃect on the result, and DMSO
was ꢀound to be the best solvent (Table 2, Entry 5). Other
solvents such as DMF, DMI and DMAC all gave worse
results (Table 2, entries 10–12). Then, diꢃerent types
and amounts oꢀ reducing agents were inspected. Increas-
ing the manganese powder amount ꢀrom 1 equiv. to 2
equiv. increased the yield ꢀrom 84% to 86%. Reducing
the amount oꢀ manganese powder to 0.5 equivalent led
to the lower yield oꢀ only 71% (Table 2, entries 5 and
(Table 2, entries 15–16). NaI was reported to be helpꢀul in
such reactions [50], however, the reaction yield has no sig-
niꢂcant change with 1 equiv. NaI addition (Table 2, entry
17). Thus, the best result was obtained with NiCl ·6H O
2
2
as catalyst, 1,10-phenanthroline monohydrate as ligand,
1 equivalent Mn as reducing reagent, and 84% yield oꢀ
O
O
H
2
SO
4
OH
O
HO
O
1
3–14). In order to compare with other types oꢀ reduct-
0oC,1 h
9
O
O
ants [37, 45], equivalent amount oꢀ zinc powder or iron
powder was used to replace manganese powder, and the
reaction yield dropped sharply to 11% or even no product
1 mmol
Yield: 89%
Scheme 3 Hydrolysis oꢀ diethyl adipate
1
3

Microwave-Assisted Nickel-Catalyzed Rapid Reductive Coupling of Ethyl 3-iodopropionate…
diethyl adipate can be obtained ꢀrom 3-iodopropanic acid
at 90 °C ꢀor 5 min as shown in Table 2 entry 5. The gram-
level reaction was carried out with 1 mol% catalyst, and
the yield barely decreased (Table 2, entry 18). It shows
that this method has potential industrial applications. And
microwave assisted cross-coupling is a good way to obtain
diethyl adipate ꢀrom 3-iodopropanic acid in a short time.
Here we ꢀurther demonstrated that AA can be obtained in
Table 3 Scope oꢀ the reductive coupling oꢀ alkyl halide
Yield (%)a
Entry
1
Substrate
Additive (eq)
–
conv. (%)
75
46
8
9% yield ꢀrom diethyl adipate at 90 °C ꢀor 1 h with H SO
2 4
(0.048 mol/L) (Scheme 3). This opens up a new pathway ꢀor
2
3
NaI (1)
–
>99
25
81
11
the conversion oꢀ glycerol to adipic acid.
To test the applicability oꢀ this method, other halide
substituted substrates were also used ꢀor the coupling reac-
tions. As shown in Table 3, the method showed good gen-
erality, and a variety oꢀ synthetically valuable ꢀunctional
groups were ꢀound to be compatible with this transꢀorma-
tion. First, the reactivity oꢀ diꢃerent halogenated hydrocar-
bons was tested. It was ꢀound that ethyl 3-bromopropion-
ate and ethyl 3-chloropropionate can also be dimerized to
give corresponding dimer products, but the results were
poor (Table 3, entries 1 and 3). The results were greatly
improved by simply adding 1 equivalent oꢀ NaI [50] to the
reaction. The yield oꢀ diethyl adipate ꢀrom ethyl 3-bromo-
propionate increased ꢀrom 46% to 81% and the yield oꢀ
diethyl adipate ꢀrom ethyl 3-chloropropionate climbed
4
5
NaI (1)
–
94
26
79
14
6
7
8
9
NaI (1)
–
NaI (1)
–
95
29
89
95
77
c
11
c
71
78
10
NaI (1)
>99
85
All reactions were perꢀormed on a 1 mmol scale with microwave irra-
diation in 5 min
Yields were tested by GC with n-dodecane as an internal standard
a
b
Yields were tested by GC with n-decane as an internal standard
ꢀ
rom 11% to 79% aꢀter NaI addition (Table 3, entries 2
−
and 4). This could be due to the substitution eꢃect oꢀ I as
a better leaving group. Analog oꢀ ethyl 3-iodopropionate
with longer carbon chains were also used ꢀor the coupling
reactions (Table 3, entries 5 and 6). It was also ꢀound that
the reactivity oꢀ long-chain hydrocarbons was very low
when NaI was not added, but can be signiꢂcantly improved
aꢀter NaI addition, which was also true ꢀor the long chain
iodoalkanes (Table 3, entries 7 and 8). For aryl halide,
dimeric products with very good yield can be obtained and
NaI addition can also improve the yield (Table 3, entries 9
and 10). Thereꢀore, the application scope oꢀ this reaction
was greatly improved by NaI addition.
mechanism, some control experiments were carried out.
First, no product can be detected without the Ni catalyst,
demonstrating the necessity oꢀ the Ni catalyst. In addition,
when a radical scavenger such as TEMPO (2, 2, 6, 6-tetra-
methylpiperidinyloxy) was added to the reaction system, the
reductive coupling product was not observed, indicating a
radical reaction pathway (Scheme 4). NaI could promote
the reaction probably by ꢀacilitating the radical generation.
Besides, the adduct product oꢀ TEMPO and alkyl radical
was detected by LC–MS (SCIEX, UPLC-X500RQTOF) as
showing in supporting inꢀormation (Fig. S6).
For the reductive coupling reaction, David and Diao
et al. proposed a radical-cage-rebound process [51–54],
then Hegedus and Weix et al. proposed the ꢀree radical
chain mechanism [49, 55–59]. To understand our reaction
On the basis oꢀ above experimental results and the mech-
anism proposed by Hegedus and Weix, a plausible ꢀree radi-
cal chain mechanism is depicted in the Scheme 5. First, the
nickel precatalyst 1 is reduced by Mn to ꢀorm active nickel
Scheme 4 Free radical trapping
O
O
experiment
Optimized condition
TEMPO (1.5 eq)
O
O
I
O
O
N
O
O
O
1
mmol
Not observed
Yield:7%
1
3

L. Zhang et al.
Scheme 5 Possible sequence oꢀ
X
X
Mn
coupling mechanism oꢀ halides
(L)Ni(II)
O
MnX
2
1
I
O
(
L)Ni(0)
MW
O
O
2
I
O
(
L)Ni(I)
I
6
O
4
O
O
(L)Ni(II)
O
I
O
O
3
O
O
Product
(
L)Ni(III)
O
I
O
5
O
(
0) intermediate 2. And then 2 selectively reacts with ethyl
Compliance with Ethical Standards
3
-iodopropionate to ꢀorm organic nickel (II) (3). Free radical
and organic nickel (II) (3) combine to generate the organic
Conflict of interest The authors declare no competing ꢂnancial inter-
4
est.
nickel (III) (5), which ꢀurther produces dimer product diethyl
adipate, and generates the organic nickel (II) (6), the result-
ing organic nickel (II) (6) rapidly induces the production oꢀ
ꢀ
ree radical 4 ꢀrom the halogenated substrate by using micro-
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Microwave-Assisted Nickel-Catalyzed Rapid Reductive Coupling of Ethyl 3-iodopropionate…
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