One-pot selective N-formylation of nitroarenes to formamides catalyzed by core-shell structured cobalt nanoparticles

Article abstract of DOI:10.1039/c8cc05285a

One-pot direct N-formylation of readily available nitroarenes with ammonium formate catalyzed by core-shell structured cobalt nanoparticles has been developed. A broad set of nitroarenes was successfully converted to their corresponding formamides in good to high yields with various functional group tolerance. This heterogeneous catalyst can be easily removed from the reaction medium and can be reused several times without a significant loss of reaction efficiency.

Full text of DOI:10.1039/c8cc05285a

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One-Pot Selective N-Formylation of Nitroarenes to Formamides
Catalyzed by Core-Shell Structured Cobalt Nanoparticles
Received 00th January 20xx,
Accepted 00th January 20xx
Xiaosu Dong, Zhaozhan Wang, Yanan Duan and Yong Yang*
DOI: 10.1039/x0xx00000x
www.rsc.org/
a) Traditional N-Formamide synthesis
One-pot direct N-formylation of readily available nitroarenes with
ammonium formate catalyzed by core-shell structured cobalt
nanoparticles has been developed. A broad set of nitroarenes was
successfully converted to their corresponding formamides in good
to high yields with various functional groups tolerance. This
heterogeneous catalyst can be easily removed from the reaction
medium and can be reused for several times without significant
loss in reaction efficiency.
H
O
N
NH2
Formylating agents
+
R
R
e.g. chloral, phosgene, CO
acetic formic anhydride
toxic formylating reagents, copious waste, poor atom-economy
b) Catalytic N-Formamide synthetic approaches
Formylating
reagents
CO2
+
NH2
NH2
R
R
e.g. MeOH, HCHO
HCOOH, HCOONH4
reductants
e.g. H2, hydrosilanes,
expensive and complex noble metal catalysts,
boranes
H
N
O
expensive or complex catalysts,
harsh conditions, or low atom efficiency
R
HCOOH(NH4)
NO2
NO2
Formamides are valuable intermediates in the synthesis of
pharmaceuticals, agrochemicals, dyes, and fragrances.1 They
also serve as industrial solvents and are used as Lewis bases in
catalysis.2 In addition, the formyl group is important amine
protecting groups in peptide synthesis.3 Owing to their
immense utility, the development of novel methods for the
expedient synthesis of formamides continues to be an active
area of research.
R
COOH
COOH
R
CO2 + H2
hazardous and pyrophoric metal catalysts with poor
reactivity; noble metal (Pd, Au, Rh, Pt, Ag) catalysts
noble metal catalysts under harsh conditions
c) This work
H
N
O
NO2
Co@NPC
R
HCOONH4
R
+
Readily available and inexpensive nitroarenes
Heterogeneous non-noble metal catalysis
High activity and excellent selectivity
Easy separation and reusable
Traditionally, N-Formamides synthesis is typically achieved
by the reaction of anilines with toxic and sensitive formylating
reagents, e.g. chloral, phosgene, CO, and acetic formic
anhydrides with poor atom economy and massive waste
production (Scheme 1a).4 In the past decades, transition-
metal-catalyzed N-formylation of anilines to formamides has
attracted considerable attention. A number of metal catalysts
have been developed for N-formylation of anilines with
various formylating reagents such as methanol,5a-c formic acid
and its derivatives,5d-g or (para)formaldehyde.5h-j Remarkably,
the catalytic N-formylation of anilines by using CO2 as a
carbonyl source together with varying reductants, e.g. H2,6
hydrosilanes,7 or boranes,8 in the presence of metal-based
catalysts has also been demonstrated. However, expensive or
complex noble metal complexes are often employed, in which
relatively harsh conditions are generally required,
Scheme 1. Traditional versus Proposed N-Formylation
or large amounts of by-products are produced simultaneously
with low atom efficiency (Scheme 1b). Furthermore, aryl
amines are most frequently used as starting materials for the
synthesis of N-arylformamides among these well-developed
methods, which are generally prepared from reduction of
nitroarenes catalyzed by transition metals under high pressure
of hydrogen.9 As such, from both economic and environmental
viewpoints, there is
a strong incentive to develop an
alternative inexpensive base-metal approach for highly
efficient and selective synthesis of formamides from readily
available and inexpensive nitroarenes.
To date, only a handful of examples catalyzed by noble
metal catalysts (e.g. Pd,10 Pt,11 Au,12 Rh,13 et al) for one-pot
direct N-formylation of nitroarenes to N-formamides using
formic acid or its derivatives, or even CO2/H2 as formylating
sources have been reported (Scheme 1b). However, the high
cost and limited reserve on the earth of noble metal catalysts
accompanying with harsh reactions significantly impede their
practical applications, especially for synthesis of biologically
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Table 1. Optimization of reaction conditions.a
regarding the preparation and characterization of the catalyst
Co@NPC-800 were included in the ESI. Our previous studies
showed that the synergistic effect between Co NPs and N,P
atoms incorporated in the carbon framework dramatically
improved the catalytic performance for catalytic transfer
hydrogenation of nitroarenes and the Co@NPC-800 gave the
best outcome. As such, the Co@NPC-800 catalyst was initially
Selectivity (%)b
Solvent Time (h) Conversion (%)b
Entry
Catalyst
Reductant
(equiv.)
2a
3a
1
Co@NPC-800 HCOOH(12)
Co@NPC-800 HCOOH(10)
Co@NPC-800 HCOOH(8)
Co@NPC-800 HCOOH(6)
Co@NPC-800 HCOOH(4)
Co@NPC-800 HCOOH(3)
Co@NPC-800 HCOONH4(10)
Co@NPC-800 HCOONH4(8)
Co@NPC-800 HCOONH4(6)
Co@NPC-800 HCOONH4(4)
Co@NPC-800 HCOONH4(10)
Co@NPC-800 HCOONH4(10)
Co@NPC-800 HCOONH4(10)
Co@NPC-800 HCOONH4(10)
Co@NPC-800 HCOONH4(10)
Co@NPC-900 HCOONH4(10)
Co@NPC-700 HCOONH4(10)
24
24
24
24
24
24
12
12
12
12
12
12
12
12
4
100
100
68
THF
95
5
2
employed for N-formylation of nitrobenzene
(1a) as a
THF
90
86
48
34
21
>99
74
29
3
10
14
52
66
79
<1
26
71
97
55
13
18
78
15
26
35
0
3
THF
benchmark reaction with formic acid (HCOOH) as formylating
reagent to optimize the reaction conditions, and the
representative results are compiled in Table 1. The reactions
were performed with varying equivalent of HCOOH (with
respect to 1a) in THF at 120oC. We found that the employed
amounts of HCOOH had a critical influence on both reaction
activity and selectivity (entries 1-6). More excess of HCOOH
resulted in higher conversion of 1a with formation of N-
phenylformamide (3a) as the major product. Particularly,
complete conversion of 1a with 95% selectivity to 3a was
achieved in the presence of 12 equivalents of HCOOH (entry 1).
Similar trend for reaction efficiency and tunability in product
selectivity was also observed when ammonium formate
(HCOONH4) was used as formylating reagent instead (entries
7-10). Comparatively, HCOONH4 distinctly exhibited superior
efficiency to HCOOH and exclusive selectivity to 3a was
realized when using 10 equivalents of HCOONH4 within 12 h
under identical conditions (entry 7).
4
30
THF
5
28
THF
6
20
THF
7
100
100
100
97
THF
8
THF
9
THF
10
11
12
13
14
15
16
17
18c
19d
20
THF
100
100
100
100
100
79
Toluene
1,4-Dioxane
CH3CN
DMF
THF
45
87
82
22
85
74
65
0
4
THF
4
37
THF
NPC-800
HCOONH4(10)
HCOONH4 (10)
12
12
12
0
THF
_
0
THF
0
0
Co(NO3)2.6H2O HCOONH4(10)
0
THF
0
0
aReaction condtions: nitrobenzene (0.25 mmol), HCOOH or HCOONH4
as formylating reagent with different equivalents with respect to
nitrobenzene, catalyst (4.8 mol% of Co), solvent (2.5 mL), 120oC.
bConversion and selectivity were determined by GC using dodecane as
an internal standard.c20 mg of the NPC support instead. dno catalyst.
Inspired by these findings, a set of factors including solvent,
temperature, amount of catalyst loading was intensively
screened. Among the solvents investigated (entries 11-14),
THF showed the best catalytic performance with complete
conversion and exclusive selectivity to 3a after 12 h (entry 7).
A decrease of the reaction temperature or catalyst loadings led
to a lower catalytic activity and selectivity to 3a (Table S1 & 2,
Figure S2 in the ESI). Subsequently, the resultant catalysts
pyrolyzed at 700 and 900oC were employed for the reaction,
respectively, under otherwise identical conditions (entries 15-
17). In line with our previous observations,14 the Co@NPC-800
significantly outperformed in terms of both activity and
selectivity of the desired product (entries 15-17). Moreover,
the catalyst Co@NPC-800 is essential for the success of the N-
formylation reaction. No reactivity was observed in the
absence of catalyst or with PNC-800 or Co(NO3)2 as catalyst
(entries 18-20).
active compounds due to the toxicity of noble metals.
Nonetheless, no successful one-pot direct N-formylation of
nitroarenes to formamides catalyzed by heterogeneous base
metals has been descried, to the best of our knowledge.
In our continuous effort to develop green catalysis for
sustainable organic synthesis, we herein report
a
heterogeneous core-shell structured cobalt nanoparticles
(NPs) catalyst for one-pot direct N-formylation of nitroarenes.
The catalyst exhibits outstanding catalytic performance for
formamides synthesis from the reductive N-formylation of
nitroarenes with ammonium formate under mild conditions. A
broad set of nitroarenes bearing with diverse functional
groups could be efficiently converted to formamides in decent
Further control experiments reveal that (1) this one-pot
to high yields. In addition, the catalyst can be easily recovered direct N-formylation of nitroarenes undergoes successive
reduction of nitro group to amine and formylation of amine to
N-formamide; (2) HCOOH or HCOONH4 serves as both a
reducing and formylating reagent. We performed the reaction
by adding 10 equivalents of HCOONH4 batch-by-batch into the
THF solution of 1a under the standard conditions as shown in
Figure 1A. 43% conversion of 1a was exclusively reduced to
aniline (2a) upon addition of first batch 3 equivalents of
HCOONH4 for 6 h, clearly indicating that HCOONH4 firstly
serves as a reducing reagent to facilitate reduction of nitro
group. After another batch 4 equivalents of HCOONH4 was
added into the above reaction mixture, 1a was further
for successive uses with negligible loss in activity,
demonstrating strong stability. To the best of our knowledge,
this is the first report of direct and selective synthesis of
formamides from readily available and inexpensive nitroarenes
and ammonium formate catalyzed by a heterogeneous non-
noble base-metal catalyst (Scheme 1c).
The heterogeneous catalysts comprising of Co NPs as core
and N,P-dual doped hierarchical porous carbon as shell derived
from naturally renewable biomass, denoted as Co@NPC-T
(where
T represents the pyrolysis temperature), were
synthesized by
a
facile tandem hydrothermal-pyrolysis consumed but affording a mixture of 2a and 3a with 3a as
major product. Accordingly, the addition of rest batch 3
processes as reported in our earlier work,14 the details
2 | J. Name., 2012, 00, 1-3
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equivalents led to 90% conversion of 1a with 83% distribution Table 2. Substrate scopea
of 3a. Such observations were further confirmed by the record
Co@NPC-800
(20 mg, 4.8 mol% Co)
NHCHO
NO2
of the product distribution as a function of reaction time
R
R
HCOONH4
+
(Figure 1B, Figure S2 in the ESI). Sole formation of 2a was
observed at the early stage of the reaction; while 3a started to
form gradually with an elapse of reaction times and dominated
the reaction at the late stage until exclusive formation.
Meanwhile, the reduction of nitrobenzene catalysed by the
Co@NPC-800 catalyst is significantly faster than N-formylation.
THF, 120oC, 12 h
2a-w
1a-w
NHCHO
NHCHO
NHCHO
CH3
NHCHO
H3C
CH3
2a
(98%)
2b (98%)
2c
2d (80%)
(94%)
NHCHO
NHCHO
OH
NHCHO
NHCHO
HO
H3CO
OCH3
2f (89%)
2g
(95%)
2e (98%)
NHCHO
2h (96%)
NHCHO
NHCHO
NHCHO
Cl
Br
Cl
Cl
2l
(82%)
NHCHO
2i
2k
(12%)
(89%)
NHCHO
2j (68%)
NHCHO
Br
(53%)b
NHCHO
F
I
Br
2o
(82%)
2p (75%)
NHCHO
2n
(16%)
2m (67%)
(57%)b
NHCHO
NHCHO
NHCHO
OHC
NC
H3COC
F3C
2s
(31%)
(47%)c
NHCHO
Figure 1. The product distributions for (A) with batch addition of
HCOONH4 and (B) as a function of reaction time for N-formylation of
nitrobenzene with HCOONH4 under standard conditions.
2r (46%)
NHCH2OH
2t
2q (39%)
(56%)c
(39%)
(57%)c
NHCHO
H3COOC
N
NHCHO
N
2w
2u (37%)
(69%)c
2x (67%)
It took 4 h to fully consume 1a while 12 h was required for
complete formation of 3a. It has been reported that the
ammonium formate mediated N-formylation of anilines took
place readily in acetonitrile at reflux temperature without
assistant of any metal catalyst.15 No significant difference in N-
formylation reaction efficiency could be observed when 2a
was subjected to the standard conditions in the absence or
presence of Co@NPC-800, indicating that there is no
accelerating effect of the Co@NPC-800 catalyst in N-
formylation of aniline (Scheme S1 in the ESI). Such result
demonstrates the essential role of the Co@NPC-800 is to
reduce nitroarenes to anilines in the whole process.
Subsequently, we investigated the substrate scope to
explore the general applicability of this catalytic N-formylation
protocol under the optimized conditions (Table 2). Overall, the
catalyst Co@NPC-800 enabled the N-formylation of a diverse
array of functionalized nitroarenes, providing the
corresponding formamides in decent to high yields. Electron-
(50%)
(84%)c
2v (45%)
(78%)c
aReaction conditions: nitroarenes (0.25 mmol), Co@NPC-800 (20 mg,
4.8 mol% of Co), HCOONH4 or HCOOH (2.5 mmol), THF (2.5 mL); 120
°C, 12 h. Yields of isolated products are reported. bHCOOH (20
equivalents) as hydrogen donor and formylating source. cHCOOH (10
equivalents) as hydrogen donor and formylating source.
excellent chemoselectivity of the nanostructured core-shell
cobalt NPs catalysts. In addition, heteroatom-containing
nitroarenes (1w and 1x) can also be efficiently formylated to
their corresponding formamides, which are in particular
important intermediates in the pharmaceutical industry.
Notably, a considerable higher selectivity to formamide was
achieved when HCOOH was used as the formylating reagent
instead of HCOONH4 in some cases; especially for para-Cl- and
Br-substituted nitrobenzenes (1k and 1n), more excess of
HCOOH (20 equivalents) is required to achieve satisfactory
results. Note that in all cases listed in Table 2, all nitroarenes
were completely converted but with different selectivity to
their corresponding N-formamides, as shown in Table S4 in the
ESI.
Durability and recyclability of a catalyst are important
features for the advancement of sustainable practical
processes. Upon completion of the N-formylation of
nitrobenzene, the catalyst Co@NPC-800 was recollected by
centrifugation, washed and dried for subsequent cycles.
Noticeably, the Co@NPC-800 catalyst is highly stable and can
be conveniently recycled up to five times to selectively
donating groups substituted nitroarenes (1a
higher yields to their corresponding formamides than that of
electron-withdrawing groups substituted ones 1q ).
-h) generally gave
(
-u
Apparently, the para-position substituted nitroarenes
regardless of the nature of substituents showed considerably
poorer selectivity to the corresponding formamides albeit with
complete conversion (1d, 1f, 1k, and 1n). In these cases,
anilines are favourably produced as the major products, most
likely due to the steric effect. More importantly, for
halogenated nitrobenzenes (1i-p), full conversion is achieved,
giving decent to high yields to the respective formamides
without any observation of dehalogenation processes.
Gratifyingly, nitroarenes bearing readily reducible functional
groups, such as aldehyde (1r), ketone (1t), nitrile 1s), ester (1u),
and vinyl (1v) were successfully formylated to the formamides
and maintained the reducible groups untouched, highlighting
the
produce
N-phenylformamide (Figure S3 in the ESI). No
noticeable changes in the core-shell nanostructure of the
catalyst Co@NPC-800 can be observed after 5 cycles (Figure S4
& 5 in the ESI).
In conclusion, a novel hybrid nanocomposite comprising
cobalt nanoparticles as core and N,P-dual doped porous
carbon as shell is found to be a highly efficient, reusable
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Catal. Sci. Technol., 2013,
3
, 2392-2396. (e) O. Jacquet, C.
heterogeneous non-noble metal catalyst for one-pot direct N-
formylation of readily available nitroarenes with ammonium
formate, selectively affording versatile and biologically active
formamides. This study provides a green and sustainable
methodology for expedient synthesis of formamides from nitro
compounds under mild conditions.
The authors would like to acknowledge the financial support
from QIBEBT, DICP & QIBEBT (Grant No. DICP& QIBEBT
UN201704), and Dalian National Laboratory for Clean Energy
(DNL), Chinese Academy of Sciences.
Das Neves Gomes, M. Ephritikhine, T. Cantat, J. Am. Chem.
Soc., 2012, 134, 2934-2937. (f) S. Das, F.D. Bobbink, S. Bulut,
M. Soudani, P.J. Dyson, Chem. Commun., 2016, 52, 2497-
2500. (g) X. Frogneux, O. Jacquet, T. Cantat, Catal. Sci.
Technol., 2014, 4, 1529-1533.
8
9
V. B. Saptal, T. Sasaki, B. M. Bhanage, ChemCatChem, 2018,
DOI: 10.1002/cctc.201800185.
(a) A. Corma, Serna, P. Science, 2006, 313, 332-334. (b) H. U.
Blaser, H. Steiner, M. Studer, ChemCatChem, 2009, 1, 210-
22; (c) R. V. Jagadeesh, A.-E. Surkus, H. Junge, M.-M. Pohl, J.
Radnik, J. Rabeah, H. M. Huan, V. Schunemann, A. Brückner,
M. Beller, Science, 2013, 342, 1073-1076. (d) S. Zhang, C.-R.
Chang, Z.-Q. Huang, J. Li, Z. Wu, Y. Ma, Z. Zhang, Y. Wang, Y.
Qu, J. Am. Chem. Soc., 2016, 138, 2629-2637.
Conflicts of interest
There are no conflicts to declare.
10 (a) V. Thakur, A. Kumar, N. Sharma, A. K. Shil, P. Das, Adv.
Synth. Catal., 2018, 360, 432-437. (b) Y. Wang, Z. Zhan, Y.
Zhou, M. Lei, L. Hu, Monatsh Chem., 2018, 149, 527-533. (c)
R. B. Nasir Baig, S. Verma, M. N. Nadagouda, R. S. Varma,
Green Chem., 2016, 18, 1019-1022. (d) B. Karimi, F.
Mansouri, H. Vali, ChemPlusChem, 2015, 80, 1750-1759. (e) X.
Notes and references
1
2
(a) H. Bipp, H. Kieczka, In Ullmann’s Encyclopedia of
Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2003;
Vol. 15, pp 36-47. (b) J. R. Dunetz, J. Magano, G. A.
Weisenburger, Org. Process Res. Dev., 2016, 20, 140-177. (c)
N. V. Reddy, P. S. Kumar, P. S. Reddy, M. L. Kantam, K. R. 11 M. Li, L. Hu, X. Cao, H. Hong, J. Lu, H. Gu, Chem. Eur. J., 2011,
Reddy, New J. Chem., 2015, 39, 805-809.
(a) K. Weissermel, H.-J. Arpe, Industrial Organic Chemistry,
3rd ed., translated by C. R. Lindley, Wiley-VCH, Weinheim,
1997. (b) I. M. Downie, M. J. Earle, h. Heaney, K. F. Shuhaibar,
Tetrahedron, 1993, 49, 4015-4034. (c) S. B. Jagtap, S. B.
Tsogoeva, Chem. Commun., 2006, 4747-4748.
J. Cui, Y. Zhang, Y. Q. Deng, F. Shi, Chem. Commun., 2014, 50
,
13521-13524. (f) T. V. Pratap, S. Baskaran, Tetrahedron Lett.,
2001, 42, 1983-1985.
17, 2763-2768.
12 (a) L. Yu, Q. Zhang, S. S. Li, J. Huang, Y. M. Liu, H. Y. He, Y.
Cao, ChemSusChem, 2015, 8, 3029-3035. (b) X.-B. Lou, L. He,
Y. Qian, Y.-M. Liu, Y. Cao, K.-N. Fan, Adv. Synth. Catal., 2011,
353, 281-286.
13 J. Xiao, C. Wang, Y. Wei, J. Wu, D. Xue, Z. Liu, Z. Zhang, G.
Chen, Synlett, 2014, 25, 1295-1298.
14 Y.-N. Duan, T. Song, X.-S. Dong, Y. Yang, Green Chem., 2018,
20, 2821-2828.
15 P. G. Reddy, G. D. K. Kumar, S. Baskaran, Tetrahedron Lett.,
2000, 41, 9149–9151
3
4
5
P. G. M. Wuts, Greene’s Protective Groups in Organic
Synthesis, 5th ed., Wiley, Hoboken, NJ. 2014, pp. 991-1003.
G. A. Olah, L. Ohannesian, M. Arvanaghi, Chem. Rev., 1987, 4,
671-686.
(a) S. Tanaka, T. Minato, E. Ito, M. Hara, Y. Kim, Y.
Yamamoto, N. Asao, Chem. Eur. J., 2013, 19, 11832-11836. (b)
N. Ortega, C. Richter, F. Glorius, Org. Lett., 2013, 15
1776−1779. (c) T. Ishida, M. Haruta, ChemSusChem, 2009,
,
,
2
538-541. (d) V. K. Das, R. R. Devi, P. K. Raul, A. J. Thakur,
Green Chem., 2012, 14, 847-854. (e) J. Deutsch, R. Eckelt, A.
Köckritz, A. Martin, Tetrahedron, 2009, 65, 10365-10369. (f)
S. Kazemi, A. Mobinikhaledi, M. Zendehdel, Chin. Chem. Lett.,
2017, 28, 1767-1772. (g) I. Sorribes, K. Junge, M. Beller,
Chem. Eur. J., 2014, 20, 7878-7883. (h) O. Saidi, M. J.
Bamford, A.J. Blacker, J. Lynch, S. P. Marsden, P. Plucinski, R.
J. Watson, J. M. J. Williams, Tetrahedron Lett., 2010, 51
5804-5806. (i) N. Shah, E. Gravel, D. V. Jawale, E. Doris, I. N.
N. Namboothiri, ChemCatChem, 2014, , 2201-2205. (j) Z. Ke,
,
6
Y. Zhang, X. Cui, F. Shi, Green Chem., 2016, 18, 808-816.
(a) U. Jayarathne, N. Hazari, W. H. Bernskoetter, ACS Catal.,
6
2018, 8, 1338-1345. (b) H. Y. Liu, Q. Q. Mei, Q. L. Xu, J. L.
Song, H. Z. Liu, B. X. Han, Green Chem., 2017, 19, 196-201. (c)
T. Mitsudome, T. Urayama, S. Fujita, Z. Maeno, T. Mizugaki, K.
Jitsukawa, K. Kaneda, ChemCatChem, 2017,
P. Daw, S. Chakraborty, G. L. Y. Diskin-Posner, Y. Ben-David,
D. Milstein, ACS Catal., 2017, , 2500-2504. (e) A. Tlili, E.
Blondiaux, X. Frogneux, T. Cantat, Green Chem., 2015, 17
9, 3632-3636. (d)
7
,
157-168. (f) L. Zhang, Z. B. Han, X. Y. Zhao, Z. Wang, K. L.
Ding. Angew. Chem. Int. Ed., 2015, 54, 6186-6189. (g) X. Cui,
X. Dai, Y. Zhang, Y. Deng, F. Shi, Chem. Sci., 2014,
(a) C. Xie, J. L. Song, H. R. Wu, B. W. Zhou, C. Y. Wu, B. X. Han,
ACS Sustainable Chem. Eng., 2017, , 7086-7092. (b) R. C.
5, 649-655.
7
5
Luo, X. W. Lin, Y. J. Chen, W. Y. Zhang, X. T. Zhou, H. B. Ji,
ChemSusChem, 2017, 10, 1224-1232. (c) R. A. Molla, P.
Bhanja, K. Ghosh, S. S. Islam, A. Bhaumi, S. M. Islam,
ChemCatChem, 2017, 9, 1939-1946. (d) K. Motokura, N.
Takahashi, D. Kashiwame, S. Yamaguchi, A. Miyaji, T. Baba,
4 | J. Name., 2012, 00, 1-3
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