Abstract
A hydroxylamine modified polypropylene fibre [Pd(II)-AOFs] was synthesised and used to catalyse the Sonogashira reaction between phenylacetylene and iodobenzene. The results showed that highly efficient catalytic activity can be achieved for the cross-coupling reaction. More importantly, the reaction conditions are moderate and do not require inert gas protection. The catalyst could be readily extracted by simple operations and conveniently recycled four times without an obviously significant decrease in activity.
References
1.
Ko
J.
,
Morinaka
B. I.
, and
Molinski
T. F.
, J. Org. Chem. , 2011 , 76 , 894 .
2.
Yin
W.
,
He
C.
,
Chen
M.
,
Zhang
H.
, and
Lei
A. W.
, Org. Lett. , 2009 , 11 , 709 .
3.
Dubbaka
S. R.
,
Kienle
M.
,
Mayr
H.
, and
Knochel
P.
, Angew. Chem. Int. Ed. , 2007 , 46 , 9093 .
4.
Matsuyama
N.
,
Kitahara
M.
,
Hirano
K.
,
Satoh
T.
, and
Miura
M.
, Org. Lett. , 2010 , 12 , 2358 .
5.
Shi
W.
,
Liu
C.
, and
Lei
A.
, Chem. Soc. Rev. , 2011 , 40 , 2761 .
6.
Hajipour
A. R.
,
Nazemzadeh
S. H.
, and
Mohammadsaleh
F.
, Tetrahedron Lett. , 2014 , 55 , 654 .
7.
Valishina
E. A.
,
Fátima
M.
, and
Silva
G.
, J. Mol. Catal. A: Chem. , 2014 , 395 , 162 .
8.
Chinchilla
R.
, and
Nájera
C.
, Chem. Rev. , 2007 , 107 , 874 .
9.
Herrmann
W.A.
,
Borhm
V. P. W.
, and
Reisinger
C. P.
, J. Organomet. Chem. , 1999 , 576 , 23 .
10.
Fu
X.
,
Zhang
S.
,
Yin
G.
, and
Doris
P. S.
, Tetrahedron Lett. , 2002 , 43 , 6673 .
11.
Shultz
D. A.
,
Gwaleney
K. P.
, and
Lee
H.
, J. Org. Chem. , 1998 , 63 , 4034 .
12.
Carlos
E. D.
,
Amanda
S. S.
,
Cristiane
Y. K.
,
Carollo
C. A.
,
Hurtado
G. R.
,
Viana
L. H.
,
Barbosa
S. L.
, and
Guerrero
P. G.
Jr.
, Tetrahedron Lett. , 2011 , 52 , 4177 .
13.
Huang
H.
,
Liu
H.
,
Jiang
H.
, and
Chen
K. X.
, J. Org. Chem. , 2008 , 73 , 6037 .
14.
Novák
Z.
,
Szabó
A.
,
Répási
J.
, and
András
K.
, J. Org. Chem. , 2003 , 68 , 3327 .
15.
Elangovan
A.
,
Wang
Y.
, and
Ho
T.
, Org. Lett. , 2003 , 5 , 1841 .
16.
Mohammad
B.
,
Bahram
B.
, and
Saeideh
J.
, J. Organometal. Chem. , 2014 , 749 , 405 .
17.
Posset
T.
, and
Blümel
J.
, J. Am. Chem. Soc. , 2006 , 128 , 8394 .
18.
Mahmoud
N.
,
Mehdi
K.
, and
Ali
E.
, Tetrahedron Lett. , 2014 , 55 , 5298 .
19.
Liu
J.
,
Peng
X.
,
Sun
W.
,
Zhao
Y.
, and
Xia
C.
, Org. Lett. , 2008 , 10 , 3933 .
20.
Mateusz
K.
,
Piotr
B.
, and
Anna
N.
, J. Catal. , 2014 , 313 , 1 .
21.
Beaupérin
M.
,
Job
A.
, and
Cattey
H.
, Organometallics , 2010 , 29 , 2815 .
22.
Wu
Z.C.
,
Huang
Y.
, and
Lu
Y. N.
, Catal. Commun. , 2012 , 29 , 158 .
23.
Gallop
C. W. D.
,
Chen
M. T.
, and
Navarro
O.
Org. Lett. , 2014 , 16 , 3724 .
24.
Li
X. A.
,
Yang
F.
, and
Wu
Y. J.
J. Org. Chem. , 2013 , 78 , 4543 .
25.
Savicheva
E. A.
,
Kurandina
D. V.
,
Nikiforov
V. A.
, and
Boyarskiy
V. P.
, Tetrahedron Lett. , 2014 , 55 , 2101 .
26.
Chen
Z. W.
,
Zhu
Y. Z.
,
Ou
J. W.
,
Wang
Y. P.
, and
Zheng
J. Y.
, J. Org. Chem. 2014 , 79 , 10988 .
27.
Hu
H
,
Yang
F.
,
Weissman
Y. J. W. H.
, and
Moore
J. S.
, J. Org. Chem. , 2013 , 78 , 10506 .
28.
Finke
A.D.
,
Elleby
E. C.
,
Boyd
M.
,
Weissman
H.
, and
Moore
J. S.
, J. Org. Chem. , 2009 , 74 , 8897 .
29.
Rao
M. L. N.
,
Jadhav
D. N.
, and
Dasgupta
P.
Org. Lett. , 2010 , 12 , 2048 .
30.
Seo
J. M.
,
Park
Y. C.
,
Jeon
I.
,
Ryu
T.
,
Park
S.
, and
Lee
P. H.
, Org. Lett. , 2013 , 15 , 3358 .
