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RSC Advances
DOI: 10.1039/C5RA25209A
COMMUNICATION
Journal Name
Electronic Supplementary Information (ESI) available:
Experimental section and spectroscopic results of synthesized
propargylamines]. See DOI: 10.1039/c000000x/
[
Table 3. A comparative study of catalyst (GOꢀCu) with previously reported
catalysts in A coupling reaction in terms of TON and TOF
3
1
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En
try
catalyst
Metal
(mol
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Yield/Conv.
(%)
TON
TOF Ref.
,
(b)
8
,
4
(
5
2
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Au/IRMOF
Au
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2
3
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NAP–MgO
AuCl
Au (ꢀꢀ)
Au (5)
Au(1)
Au
96
99
100
93
407
20
100
668
17
1.7
8.3
111
26b
26c
26c
26d
(
a
2
b) T.
AuBr
3
(1)
2
2
004, 126, 5968ꢀ5969.
a
b
a
Au/ZrO
4
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(
(
(
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6
GOꢀCu
Cu
85
146
18.3
This
(
0.58)
Work
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b) D. Aguilar, M.
N
N
2 3
OCH CH
O
(
c
O
Si
N
C
H
O
d
O
Cu
H
2
O
4
AcO
6
(a
R
4
CH
2
b
R
4
CH
9
7
1
2
J
(
45; (c
d
e
N
N
OCH
2
CH
3
N
N
OCH
2
CH
3
O
O
O
Si
O
7
8
a
,
O
Si
N
C
O
N
C
H
H
b
,
O
H
H
2
O
Cu
O
Cu
H
2
O
c)
G. Villaverde, A. Corma, M. Iglesias and F.
OAc
GO-Cu
AcO
Saanchez, ACS Catal., 2012,
) S. Kumari, A. Shekhar and D. D. Pathak, RSC Adv., 2014,
1187–61192; ( ) a) S. S. Li, J. J. Lv, Y. Y. Hu, J. N. Zheng, J. R.
2, 399−406.
R
4
C
(
6
a
4,
b
-H
2
O
N
N
2 3
OCH CH
O
O
Chen, A. J. Wang and J. J. Feng, J. Power Sources, 2014, 247, 213–
218.
Y. L. Min, K. Zhang, W. Zhao, F. C. Zheng, Y. C. Chen and Y. G.
Zhang, Chem. Eng. J., 2012, 194, 203–210.
0 H. P. Mungse, S. Verma, N. Kumar, B. Sain and O. P. Khatri, J.
Mater. Chem., 2012, 22, 5427–5433.
O
Si
N
C
H
R
2
R
3
N
O
Cu
C
9
1
1
1
1
2
H O
R
1
R
4
AcOH
-AcOH
R
4
1 H. Su, Z. Li, Q. Huo, J. Guan and Q. Kan, RSC Adv., 2014,
9996.
4, 9990–
O
R
2
R
3
R
1
N
H
R
2
+
+
N
C
H
R
1
R
3
2 S. Verma, M. Aila, S. Kaul and S. L. Jain, RSC Adv., 2014,
0604.
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4, 30598–
3
Scheme 3. Proposed reaction mechanism for the formation of
propargylamines
3
3
1
a
.
Conclusions
Piccinini, S. J. Freakley, J. C. Pritchard, J. K. Edwards, A. F. Carley
and G. J. Hutchings, Green Chem., 2012, 14, 170ꢀ181.
S. Kumari, A. Shekhar, H. P. Mungse, O. P. Khatri and D. D. Pathak,
RSC Adv., 2014, 4, 41690–41695.
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2
Herdtweck, Dalton Trans., 2000, 3570–3574; (c) P. K. Khatri, S.
Choudhary R. Singh, S. L. Jain and O. P. Khatri, Dalton Trans., 2014,
4
In summary, we have developed a new Cu(II) Schiff base
complex immobilized onto graphene oxide and demonstrated its
catalytic application in the green synthesis of propargylamines from
aldehydes, alkynes and amines without using any base or coꢀcatalyst
in aqueous medium . The developed catalyst is very cheap, easily
recovered at the end of the reaction, and recycled up to four times
without significant loss in catalytic activity.
1
1
5
6
011, 25, 54–60; (b) M. Santos, F. E. Kuhn, W. M. Xue and E.
3, 8054–8061; (d) R. Nie, J. Wang, L. Wang, Y. Qin, P. Chen and Z.
Notes and references
Department of Applied Chemistry, Indian School of Mines, Dhanbadꢀ
Hou, Carbon, 2012, 50, 586–596.
a
17 (a) M. Ozdemir, Inorganica Chimica Acta, 2014, 421, 1–9; (b) A.
Stuart, Infrared Spectroscopy: Fundamentals and Applications, J. Wiley,
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8
b
26004, India
Department of Chemistry, Vidya Vihar Institute of Technology, Purneaꢀ 18 Anuradha, S. Kumari and D. D. Pathak, Tetrahedron Lett., 2015, 56,
135–4142.
54303, India
4
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(a) K. Nakamoto, Coordination Compounds. In Infraed and Raman
Spectra of Inorganic and Coordination Compounds, 4th Ed.; John Wiley
and Sons, Inc.: New York, 1986. (b) Z. Li, S. Wu, H. Ding, D. Zheng, J.
Hu, X Wang, Q. Huo, J. Guan and Q. Kan New J. Chem., 2013, 37,
Email: Shweta@ac.ism.ac.in (Shweta Kumari), amiyashekhar@gmail.com
Phone number: +91 9431126250
(
*
1
561ꢀ1568.
We are thankful to the CRF ISM, SAIF IIT Madras, SAIF Panjab
University, STIC, Kochi, and IISER Bhopal for providing help in
the analysis of the samples. SK acknowledges the receipt of ISM
fellowship.
2
0
Z. Li, S. Wu, H. Ding, H. Lu, J. Liu and Q. Kan, New J. Chem., 2013,
37, 4220—4229.
4
| J. Name., 2012, 00, 1-3
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