Recyclable heterogeneous iron supported on imidazolium ionic liquid catalysed palladium and copper-free Heck reaction

Article abstract of DOI:10.1016/j.jorganchem.2021.122073

A natural friendly iron-immobilized on imidazolium supported ionic liquid [Gmim]Cl-Fe (III) was effectively evaluated as a heterogeneous catalyst for Mizoroki-Heck reaction with good to excellent yield under solvent free condition. [Gmim]Cl-Fe (III) showed good activities that were comparable to that of palladium catalysts. Furthermore, this phosphine, copper and palladium- free catalyst was simply recovered from the reaction mixture and recycled seven times.

Full text of DOI:10.1016/j.jorganchem.2021.122073

Journal of Organometallic Chemistry 954–955 (2021) 122073
Contents lists available at ScienceDirect
Journal of Organometallic Chemistry
journal homepage: www.elsevier.com/locate/jorganchem
Recyclable heterogeneous iron supported on imidazolium ionic liquid
catalysed palladium and copper-free Heck reaction
Manickam Deepaa, Uthayanila Selvarasub, Kolanjinathan Kalaivanic,
Karthikeyan Parasuramana,∗
a PG and Research Department of Chemistry Pachaiyappas College Campus, University of Madras Chennai-600 030, Tamilnadu, India
b Department of Chemistry, Pachaiyappas College for Women Campus, University of Madras, Kanchipuram - 631501 Tamilnadu, India
c Department of Chemistry, Dhanalakshmi Srinivasan College of Arts and Science for Women, Preambular 621 212, Tamil Nadu, India
a r t i c l e i n f o
a b s t r a c t
Article history:
A natural friendly iron-immobilized on imidazolium supported ionic liquid [Gmim]Cl-Fe (III) was effec-
tively evaluated as a heterogeneous catalyst for Mizoroki-Heck reaction with good to excellent yield un-
der solvent free condition. [Gmim]Cl-Fe (III) showed good activities that were comparable to that of pal-
ladium catalysts. Furthermore, this phosphine, copper and palladium- free catalyst was simply recovered
from the reaction mixture and recycled seven times.
Received 25 May 2021
Revised 27 August 2021
Accepted 2 September 2021
Available online 4 September 2021
© 2021 Elsevier B.V. All rights reserved.
Keywords:
Green chemistry
Iron catalysis
Mizoroki-Heck reaction
Ionic liquid
1. Introduction
environmentally friendly, functional group tolerance, scalability for
large scale procedures in addition Fe (III) catalysts are air-moisture
The Mizoroki-Heck coupling reaction represents one of the
most appreciated methods for Csp2-Csp2 bond-forming reactions
in organic synthesis [1–6]. However, traditional Heck reaction in-
volves in central tool for the structure of current pharmaceuti-
cal, fine chemicals syntheses/ intermediates and antioxidants agro-
chemical [1–6]. Furthermore, existed method gained increasing im-
portant both in large scale industrial processes as well as for the
progress of new materials and biologically active compounds [7–
8]. But in the other hand, those synthetic protocol suffers from
the inherent drawback an expensive metal catalyst, metal leading,
catalyst reuse, economy and accompanied formation of a stoichio-
metric amount of hazardous halide salt, which can cause signifi-
cant environmental concerns [7–8]. Henceforth, the development
of economic-environmental, toxic-free recycling catalytic systems
is need for the Mizoroki-Heck coupling reactions from both aca-
demic and industrial perspectives.
stable and easy to store for long periods under normal laboratory
conditions. Nevertheless, only limited reports are available on the
iron catalysed Heck reaction.
The recent report by Hajipour and Azizib on iron-catalyzed
Heck reaction for selective olefination of aryl iodides in PEG
[26]. After that, several catalytic approaches under (palladium–
poly(N–vinylpyrrolidone)–iron) [28], FeCl2/t-BuOK/DMSO [27],
Fe(OTf)2/TBPB [29] and silica- supported iron (III) [30] conditions
were developed for iron catalyzed Heck type coupling reactions.
To the best of our knowledge, an overall and resourceful iron-
functionalized 1-glycyl-3-methyl imidazolium chloride, catalysed
for the arylation of olefins by the Mizoroki-Heck reaction has not
been developed to date. Hence, we first report a simple, stable, se-
lective, cost-effective, environmentally benign, suitable ligand that
leads to efficient heterogeneous iron complex and re-processibility
(Ionic liquids were chosen because of their recyclability and
reusability) catalytic system for the Heck reaction of aromatic
halogens and styrene under solvent free conditions (Scheme 1).
However, catalyst recovery and metal leaching can occur in the
extractive work up leading to a damage of the metal catalyst in
the reactant mixture on the one side requests additional effort to
purify the extracted product. To overcome such issue, novel iron
complex was developed by covalent linking of chloroglycine unit
with an imidazolium moiety. This tells a low solubility of catalyst
in the molecular/ organic solvents used for extraction of the prod-
In the recent years, to finding suitable catalytic systems for the
heck reaction involving other than palladium metals such as Ni [9–
10], Co [11–16], Ru [17–19], Rh [20–22], Cu [23–25], and Fe [26–
29] have also been received considerable attention. Among them,
iron is one of the most abundant metals on earth, inexpensive,
∗
Corresponding author.
E-mail address: pkarthikeyan99@gmail.com (K. Parasuraman).
https://doi.org/10.1016/j.jorganchem.2021.122073
0022-328X/© 2021 Elsevier B.V. All rights reserved.

M. Deepa, U. Selvarasu, K. Kalaivani et al.
Journal of Organometallic Chemistry 954–955 (2021) 122073
Table 1
Influence of the base on Heck coupling reaction.a
Entry
Base
Time (h)
Yieldb (%)
TON
TOFf
1
–
24
24
24
24
24
24
24
24
24
24
12
06
04
03
04
04
Trace
25
26
50
51
35
31
10
17
94
94
94
94
90
94
90
–
–
2
Na2CO3
K2CO3
NaOH
KOH
5000
5200
10000
10200
7000
6200
2000
3400
18800
18800
18800
18800
18000
18800
18000
208
217
417
425
292
258
83
3
4
5
6
NaOAc
KOAc
Cs2CO3
LiOH
Et3N
Scheme 1. Mizoroki-Heck cross-couplings of substituted aryl halides with styrene.
7
8
9
141
783
1566
3133
4700
6000
4700
4500
10
11
12
13
14
15
16
uct on the one view and high solubility in the reaction medium on
the other views [31]. This approach was applied to Heck reaction
providing high yield and good recyclability of the [Gmim]Cl-Fe (III)
catalyst.
Et3N
Et3N
Et3N
Et3Nc
Et3Nd
Et3Ne
2. Experimental
a
Reaction condition: Iodobenzene (1 mmol), styrene (1.2
mmol), different base (2 mmol), and [Gmim]Cl-Fe (III) (0.005
mol%) stirring at 80°C.
2.1. Materials and methods
b
Yield determined by HPLC.
All solvents and chemicals were commercially available and
used without further purification unless otherwise stated. The 1H-
NMR spectra were recorded on a Bruker 300 MHz using CDCl3/
DMSO-d6 as the solvent and mass spectra were recorded on JEOL
GC MATE II HRMS (EI) spectrometer. FT-IR was recorded on AVA-
TRA 330 spectrometer with DTGS detector. Column chromatogra-
phy was performed on silica gel (200-300 mesh). Analytical thin-
layer chromatography (TLC) was carried out on precoated silica gel
GF-254 plates.
c
Time (3 h).
d
Conc. of Et3N (2.5 mmol).
e
Conc. of Et3N (1.5 mmol).
TOF-turnover frequency (mol product per mol catalyst h−1).
f
NMR (75 MHz, CDCl3): δ 124.4, 124.6, 126.7, 126.9, 127.2, 128.5,
130.4, 130.8, 132.6, 133.9, 137.5 and 145.3.
2.3.5. 4-Cyano-trans-stilbene (4d)
[33–34]; 76% yield. 1H-NMR (300 MHz, CDCl3): δ 7.01 (d, J=
16.3 Hz,1H), 7.15 (d, J= 16.5 Hz, 1H), 7.25-7.30 (m, 3H) and 7.45-
7.55 (m, 6H); 13C-NMR (75 MHz, CDCl3): δ 112.5, 121.0, 127.6, 127.7,
127.9, 129.4, 129.8, 133.5, 133.7, 137.7 and 140.9.
2.2. Preparation of [Gmim]Cl-Fe (III) complex
[Gmim]Cl-Fe (III) complex was reported recently in our group
[32].
2.4. Recycling of the catalyst for the model reaction of iodobenzene
2.3. Procedure for Heck reaction
with styrene using [Gmim]Cl-Fe (III) under solvent free condition
In a 100 mL conical flask, a mixture of substituted haloben-
zene (1 mmol), styrene (1.2 mmol), triethylamine (2 mmol) and
[Gmim]Cl-Fe (III) (0.005 mol %) was added and stirred at 80°C for
a period as indicated in Table 4 (The reaction was monitored by
HPLC and TLC). The resulting heterogeneous mixture was extracted
with ethyl acetate or diethyl ether (3 × 5 mL). The organic phase
was separated and dried over anhydrous Na2SO4 and evaporated.
The resulting crude was purified by column chromatography to
give the desired pure product with excellent yield.
trans-Stilbene (4a) [33–34]; 94% yield. 1H-NMR (300 MHz,
CDCl3): δ 7.03 (s, 2H), 7.15-7.20 (m, 2H), 7.32 (t, J= 7.5 Hz, 4H) and
7.45 (d, J=7.5 Hz, 4H); 13C-NMR (75 MHz, CDCl3): δ 125.4, 128.2,
130.1 and 136.3.
Iodobenzene (1 mmol) was reacted with styrene (1.2 mmol)
in the presence of [Gmim]Cl-Fe (III) (0.005 mol%) and triethy-
lamine (2 mmol) at 80°C. After completion of the reaction (TLC/
HPLC), the product was extracted as stated in the preceding gen-
eral method. The brown solid [Gmim]Cl-Fe (III) was isolated by
centrifugation. Furthermore, the recovered complex was washed
with diethyl ether and dried in air. The resulting catalyst was
charged to another batch of the similar reaction. This was repeated
for 7 runs to complete the reaction in 4 hours to give the desired
product with 94-87 % yield (Table 5).
3. Results and discussion
p-Methyl-trans-stilbene (4c) [33–34]; 87% yield. 1H-NMR (300
MHz, CDCl3): δ 2.33 (s, 3H), 7.00 (s, 2H), 7.10 (d, J=8.3 Hz, 2H),
7.18-7.24 (m, 1H), 7.30 (t, J=7.5 Hz, 2H), 7.37 (d, J=8.3 Hz, 2H) and
7.46 (d, J=7.5 Hz, 2H); 13C-NMR (75 MHz, CDCl3): δ 21.0, 127.5,
127.6, 128.0, 128.4, 129.5, 130.3, 135.8, 138.4 and 138.5.
To get information on the optimal catalyst conditions, we car-
ried out intensive examinations to define the suitable base for this
coupling reaction. Nine different bases were tested for 24 to 04
hours using 0.005 mol% catalyst. Table 1 shows the data collected
for the synthesis of (E)-1,2-diphenylethene as a model reaction.
Primarily, trace amount of product was occurred when the absence
of base (Table 1, entry 1). Though, reaction was carried using nu-
merous bases with 10-51% yields (Table 1, entries 2-9). Moreover,
Et3N is superior in evaluation to various bases (Table 1, entry 10).
we further optimized the reaction conditions in presence of Et3N.
The trials showed that on decreasing the time from 24 to 04 hours
gave the same results (Table 1, entries 11-13). Then the yields were
dropped significantly on decreasing the time from 04 to 03 hours
(Table 1, entry 14). Supplementary when the amount of the base
was increased from 2 to 2.5 mmol, the yield was not improved
(Table 1, entry 15) in the other hand dissimilar yield was achieved
2.3.3. p-Methoxy-trans-stilbene (4b)
[33–34]; 95% yield. 1H-NMR (300 MHz, CDCl3): δ 3.75 (s, 3H),
6.80 (d, J=8.3 Hz, 2H), 6.94 (d, J=15.9 Hz, 1H), 7.00 (d, J=16.6 Hz,
1H), 7.13-7.29 (m, 4H) and 7.40-7.46 (m, 3H); 13C-NMR (75 MHz,
CDCl3): δ 54.5, 115.2, 126.3, 126.2, 127.7, 127.9, 129.0, 129.3, 131.2,
138.7 and 160.6.
2.3.4. 4-Nitro-trans-stilbene (4e)
[33–34]; 78% yield. 1H-NMR (300 MHz, CDCl3): δ 5.53 (s, 1H),
5.57 (s, 1H), 7.24-7.44 (m, 5H), 7.56 (d, 2H) and 8.19 (d, 2H); 13C-
2

M. Deepa, U. Selvarasu, K. Kalaivani et al.
Journal of Organometallic Chemistry 954–955 (2021) 122073
Table 2
Table 3
Impact of the various catalysts on Heck coupling reaction.a
Effect of the solvent on the Heck coupling reaction.a
Entry
Solvent
Time (h)
Yieldb (%)
TON
TOFe
Entry
Catalyst
Time (h)
Yieldb
TON
TOFi
1
n-heptane
p-xylene
Toluene
EtOH
24
24
24
24
24
24
24
24
24
24
04
04
04
24
Trace
Trace
Trace
Trace
Trace
Trace
49
–
–
1
–
24
24
24
24
24
24
24
24
24
24
24
04
04
04
05
03
04
04
Trace
20
17
32
37
13
18
26
52
59
67
94
94
91
94
92
94
92
–
–
2
–
–
2
FeBr2
40
2
3
–
–
3
FeCl2
34
1
4
–
–
4
FeCl3
64
3
5
MeOH
–
–
5
FeBr3
74
3
6
DCM
–
–
6
[Cemim]Br
26
1
7
1,4 dioxane
DMF
9800
6400
8800
9600
18800
18800
18000
9000
408
267
367
400
4700
4700
4500
375
7
[Aemim]Br
36
1
8
32
8
[Gmim]Cl
52
2
9
CHCl3
44
9
FeCl3/[Cemim]Br
FeCl3/[Aemim]Br
FeCl3/[Gmim]Cl
[Gmim]Cl-Fe (III)
[Gmim]Cl-Fe (III)c
[Gmim]Cl-Fe (III)d
[Gmim]Cl-Fe (III)e
[Gmim]Cl-Fe (III)f
[Gmim]Cl-Fe (III)g
[Gmim]Cl-Fe (III)h
104
118
134
18800
15666
22750
18800
18400
18800
18400
4
10
11
12
13
14
DMSO
48
10
11
12
13
14
15
16
17
18
5
Solvent free
Solvent freec
Solvent freed
Water
94
6
94
4700
3917
5687
3760
6133
4700
4600
90
45
a
Reaction condition: Iodobenzene (1 mmol), styrene (1.2 mmol), Et3N
(2 mmol), Solvent (3 mL), and [Gmim]Cl-Fe (III) (0.005 mol%) stirring at
80°C.
b
Yield determined by HPLC.
c
a
Temperature (85°C).
Temperature (75°C).
TOF-turnover frequency (mol product per mol catalyst h−1).
Reaction condition: Iodobenzene (1 mmol), styrene (1.2 mmol), Et3N
(2 mmol), and different catalyst (Entry (2-11) catalyst Conc. (0.005
mmol), (entry 12 and 15-18) (0.005 mol%) stirring at 80°C.
d
e
b
Yield determined by HPLC.
C
Catalyst concentration (0.006 mol%).
d
Catalyst concentration (0.004 mol%).
when decreasing the base amount from 2 to 1.5 mmol (Table 1,
entry 16). By all these study results, it was concluded that 2 mmol
Et3N is sufficient to brought out the complete Heck reaction in 04
hours at 80°C.
e
Time (5 h).
f
Time (3 h).
g
Temperature (85°C).
h
Temperature (75°C).
TOF-turnover frequency (mol product per mol catalyst h−1).
i
Our next goal was to find an appropriate solvent for the synthe-
sis of (E)-1,2-diphenylethene. According to publications from Vogel
and co-workers [27], Bao [29] and Joshaghani [28] polar, aprotic
solvents tend to give the best results for the Heck reaction, while
Hajipour [26] obtained high-activity of catalysts in PEG-200 sol-
vent. Among the previous reports, catalysis in absence of solvent
was the most productive, as compared with the polar and non-
polar solvents (Table 2, entries 1-11). This may be due to the easy
coordination of complex with organic co-solvents. However, tem-
perature also plays a significant role in the model reaction. When
we conducted the heck reaction at 85°C, there was no change in
the yield (Table 2, entry 12) but in the case of 75°c decrease in the
coupling product (Table 2, entry 13). Furthermore, it has also been
reported that water molecule sometimes is essential to activate the
Fe (III) complex. In our case, the coupling reaction in water gave a
negative effect on the yield in comparison with solvent free condi-
tion (Table 2, entry 14). This lower yield could be due to complex
delocalization under aqueous condition.
ture of FeCl3 and the different ionic liquids led to significant activ-
ity to the model reaction (Table 3, entries 9-11). However, among
them heterogeneous [Gmim]Cl-Fe (III) catalyst was found to be the
best catalyst providing 94 % yield in 04 hours (Table 3, entry 12).
Afterwards, parallel yield was reached when rising the catalyst
amount from 0.005 to 0.006 mol% (Table 3, entry 13) and it was
found that the amount product decreases with decrease in catalyst
loading (Table 3, entry 14). next, the reaction duration was further
optimized. The results showed that on increasing the time from
04 to 05 hours gave the same (Table 3, entry 15). However, the
yields were dropped significantly on decreasing the time from 04
to 03 h (Table 3, entry 16). In contrast to other protocols, when the
reaction was performed at a higher temperature (85°C) could not
increase the yield of product (Table 3, entry 17). However, a lower
temperature (75°C) only a 92% of product was detected (Table 3,
entry 18).
In general, catalytic reactions which can be carried out with a
small amount of in-expensive metal complexes is the most use-
ful feature for the Heck coupling. According to publications, Ha-
jipour and Azizi attained 85% yield in the heterogeneous iron cat-
alyst for selective olefination of aryl iodides in PEG-200 stirred at
130°C for 1-6 hours [26]. Using FeCl2/t-BuOK/DMSO in the range
between 20 to 80 %, Vogel et al., detected satisfactory rate in the
Heck reaction [27]. Among the earlier data’s, increasing the quan-
tity of the catalyst can improve the reaction yield and shorten re-
action time. We next examined the reaction conditions for a spe-
cific catalyst the coupling reaction was performed in presence of
Et3N by using diverse catalysts and the results are given in Table 3.
Unfortunately, (E)-1,2-diphenylethene was not detected in the ab-
sence of catalyst (Table 3, entry 1). To our delight, when using
a various iron salts, the coupling reaction gave the desired cou-
pling product either in traces or in lower yields (Table 3, en-
tries 2-5). Next, we tested the activity of synthesized 1-carboxy
ethyl-3-methyl imidazolium bromide [Cemim]Br, 1-(2-aminoethyl)-
3-methylimidazolium bromide [Aemim] Br, 1-glycyl-3-methyl imi-
dazolium chloride [Gmim]Cl, 13-26% yield of the coupling product
was obtained (Table 3, entries 6-8). Furthermore, we tried the mix-
With suitable conditions in hand, we studied the scope and
limitations of this [Gmim]Cl-Fe (III) catalysed Csp2-Csp2 coupling
reaction (Table 4). All reactions were carried out using 0.005
mol% catalyst at 80°C in the presence of 2 equiv. of NEt3. More
specifically, para-methoxy substituted iodobenzene gave the cou-
pling product in excellent yield (Table 4, entry 2). Likewise, para-
methyl and para-cyno substituted aryl iodides were successfully
converted in 87-90 % yields (Table 4, entry 3-4). In addition, aryl
chloride showed moderate reactivity with other activated substi-
tuted groups such as para-(nitro/ methoxy/ methyl/cyno) and af-
forded the corresponding coupling products in moderate to good
yields (Table 4, entry 6-9). Similarly, functionalized aryl bro-
mides containing both electron donating and electron withdraw-
ing groups felt efficient coupling reaction with styrene. However,
para- methoxy and methyl substituted aryl bromides reacted well
with styrene gave the corresponding products in reasonable to
good yields (Table 4, entry 11-12). Additionally, reasonable rela-
tively were observed, when para-chloro-aryl bromide were sub-
jected to coupling with styrene (Table 4, entry 13). Particularly, in
3

M. Deepa, U. Selvarasu, K. Kalaivani et al.
Journal of Organometallic Chemistry 954–955 (2021) 122073
Table 4
Synthesis of substituted Stilbenes.a
Entry
R
X
I
Product
Time (h)
Yield (%)
TON
TOFc
Melting point°C (lit.) [33–34]
1
H
1a
1b
1c
1d
1a
1e
1b
1c
1d
1a
1b
1c
1f
04
04
06
07
12
14
13
16
12
08
08
10
07
94
95
87
90
75
78
80
73
76
89
92
80
80
18800
19000
17400
18000
15000
15600
16000
14600
15200
17800
18400
16000
16000
4700
4750
2900
2571
1250
1114
1231
912
123-125 (122-125)
135-136 (135-137)
118-119 (118-120)
117-118 (116-118)
122-124 (122-125)
156-157 (156-157)
135-137 (135-137)
118-120 (118-120)
116-118 (116-118)
123-125 (122-125)
136-137 (135-137)
119-120 (118-120)
ND
2
p-OCH3
p-CH3
p-CN
H
3
4
5
Cl
6
p-NO2
p-OCH3
p-CH3
p-CN
H
7
8
9
1267
2225
2300
1600
2286
10
11
12
13
Br
p-OCH3
p-CH3
p-Cl
a
Reaction condition: Substituted aryl halide (1 mmol), styrene (1.2 mmol), Et3N (2 mmol), and [Gmim]Cl-Fe (III)
b
(0.005 mol%) stirring at 80°C. Yield determined by HPLC.
c
TOF-turnover frequency (mol product per mol catalyst h−1). All the products were characterized by spectro-
scopic analysis (1H-NMR) known compounds were compared with authentic data [33–34].
Table 5
all the cases, complete trans selectivity was observed and the for-
Recycling of the catalyst for the reaction of iodobenzene with
styrene.a
mations of cis or homo coupling products were not observed.
Isolation of the [Gmim]Cl-Fe (III) catalyst was easily performed
by extraction or centrifugation. The isolated catalyst was washed
with diethyl ether and dried in air. The regenerated catalyst was
used for the reaction of iodobenzene with styrene for seven
runs to afford (E)-1,2-diphenylethene with 94-87 % isolated yields
(Table 5). Hence, based on the results, a possible mechanism for
the Heck reaction is proposed, but it is clear that the mechanism is
strongly modified depending of the halobenzene employed, obtain-
ing in both cases trans-stilbene as the main product (Scheme 2)
[2].
Entry
1
2
3
4
5
6
7
Recycle No.
Yield (%)b
0
1
2
3
4
5
6
94
94
93
91
90
88
87
a
Reaction condition: Iodobenzene (1 mmol), styrene (1.2
mmol), Et3N (2 mmol), and [Gmim]Cl-Fe (III) (0.005 mol%)
stirring at 80°C.
b
Yield determined by HPLC.
Scheme 2. Proposed catalytic mechanism.
4

M. Deepa, U. Selvarasu, K. Kalaivani et al.
Journal of Organometallic Chemistry 954–955 (2021) 122073
Table 6
Comparison of catalytic activity of Iron complexes with previously reported methods in the Heck reactions.
Entry
catalyst and conditions
Time (h)
Yield (%)
Ref.
1
2
3
4
5
K2CO3 (0.5 mmol), methyl acrylate (0.3 mmol), 0.01 g of SiO2-Fe(acac)/1.5 mL PEG-200, 130°C
FeCl2 (20 mol%), picolinic acid (80mol%), t-BuOK (4 equiv.), argon (3 times), DMSO (5 mL), 60°C
Fe(OTf)2 (5 mol %), TBPB (3 mmol, 3 equiv), 1,4-dioxane (4 mL), 50°C
1.5-7
3-12
3
69-85
0-92
26
27
0-80
29
K2CO3 (1.0 mmol), H2O/EtOH (1:1) (4.0 ml), silica- supported iron (0.8 mmol) at 80°C
Et3N (2 mmol),[Gmim]Cl-Fe (III) (0.005 mol%), 80°C.
2-15
4-16
67-93
73-95
30
Present Work
To compare the efficiency of our catalyst with some of the re-
ported catalysts for the Heck reaction, we have tabulated the re-
sults of these catalysts for the synthesis of derivative Stilbene com-
pound Table 6. As shown in Table 6, our catalyst is superior to
some of the previously reported catalysts in terms of reaction con-
dition, reaction time, and yield.
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strup, Mild and efficient nickel-catalyzed Heck reactions with electron-rich
olefins, J. Am. Chem. Soc. 134 (2012) 443–452 DOI:, doi:10.1021/ja2084509.
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We have established that chloroglycine- ionic liquid imida-
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Declaration of Competing Interest
The authors declare that they have no known competing finan-
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Supplementary materials
Supplementary material associated with this article can be
found, in the online version, at doi:10.1016/j.jorganchem.2021.
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