Abstract
An amino acid was anchored to chloroacetylated polystyrene beads and the polymeric ligand containing N, O donor sites was treated with a solution of CuI to form the supported copper complex. The one-pot synthesis of propargylamines was then achieved efficiently via a three-component coupling of aldehydes, alkynes and amines using the supported copper catalyst under mild conditions. The catalyst could be recovered by simple filtration and reused several times without significant loss of activity.
References
1.
Naota
I.
,
Takaya
H.
, and
Murahashi
S.I.
, Chem. Rev. , 1998 , 98 , 2599 .
2.
Dyker
G.
, Angew. Chem., Int. Ed. , 1999 , 38 , 1698 .
3.
Wei
C.
, and
Li
C.-J.
, J. Am. Chem. Soc. , 2002 , 124 , 5638 .
4.
Tubery
F.
,
Grierson
D.S.
, and
Husson
H.-P.
, Tetrahedron Lett. , 1987 , 28 , 6457 .
5.
Murai
T.
,
Mutoh
Y.
,
Ohta
Y.
, and
Murakami
M.
, J. Am. Chem. Soc. , 2004 , 126 , 5968 .
6.
Wei
C.
, and
Li
C.-J.
, J. Am. Chem. Soc. , 2002 , 124 , 5638 .
7.
Black
D.A.
, and
Arndtsen
B.A.
, Tetrahedron , 2005 , 61 , 11317 .
8.
Yan
W.
,
Wang
R.
,
Xu
Z.
,
Xu
J.
,
Lin
L.
,
Shen
Z.
, and
Zhou
Y.
, J. Mol. Catal. A: Chem. , 2006 , 255 , 81 .
9.
Li
Z.
,
Wei
C.
,
Chen
L.
,
Varma
R.S.
, and
Li
C.-J.
, Tetrahedron Lett , 2004 , 45 , 2443 .
10.
Wei
C.
, and
Li
C.-J.
, J. Am. Chem. Soc. , 2003 , 125 , 9584 .
11.
Fischer
C.
, and
Carreira
E.M.
, Org. Lett , 2001 , 3 , 4319 .
12.
Frantz
D.E.
,
Fassler
R.
, and
Carreira
E.M.
, J. Am. Chem. Soc. , 1999 , 121 , 11245 .
13.
Zani
L.
,
Alesi
S.
,
Cozzi
P.G.
, and
Bolm
C.
, J. Org. Chem. , 2006 , 71 , 1558 .
14.
Lee
K.-Y.
,
Lee
C.-G.
,
Na
J.-E.
, and
Kim
J.-N.
, Tetrahedron Lett. , 2005 , 46 , 69 .
15.
Akullian
L.C.
,
Snapper
M.L.
, and
Hoveyda
A.H.
, Angew. Chem., Int. Ed. , 2003 , 42 , 4244 .
16.
Kuninobu
Y.
,
Inoue
Y.
, and
Takai
K.
, Chem. Lett , 2006 , 35 , 1376 .
17.
Ley
S.V.
,
Baxendale
I.R.
,
Bream
R.N.
,
Jackson
P.S.
,
Leach
A.G.
,
Longbottom
D.A.
,
Nesi
M.
,
Scott
J.S.
,
Storer
R.I.
, and
Taylor
S.J.
, J. Chem. Soc. Perkin Trans.1 , 2000 , 23 , 3815 .
18.
Wright
M.E.
, and
Pulley
S.R.
, J. Org. Chem. , 1987 , 52 , 5036 .
19.
Zhang
H.
,
Cai
Q.
, and
Ma
D.
, J. Org. Chem. , 2005 , 70 , 5164 .
20.
Ma
D.
,
Cai
Q.
, and
Xie
X.
, Synlett , 2005 , 1767 .
21.
Zhu
W.
, and
Ma
D.
, J. Org. Chem. , 2005 , 70 , 2696 .
22.
Ma
D.
, and
Liu
F.
, Chem. Commun. , 2004 , 1934 .17 B.M. Trost and D.T. Stiles, Org. Lett. , 2005, 7 , 2117.
23.
Beletskaya
I.P.
, and
Cheprakov
A.V.
, Coord. Chem. Rev. , 2004 , 248 , 2337 .
24.
Trost
B.M.
, and
Stiles
D.T.
, Org. Lett. , 2005 , 7 , 2117 .
25.
Mannich
C.
, and
Chan
F.T.
, Ber , 1933 , 66 , 418 .
26.
Ann
J.H.
,
Joung
M.J.
, and
Yoon
N.M.
, J. Org. Chem. , 1999 , 64 , 488 .
27.
Nakamura
H.
,
Kamakura
T.
,
Ishikura
M.
, and
Biellmann
J.F.
, J. Am. Chem. Soc. , 2004 , 126 , 5958 .
28.
Bieber
L.W.
, and
Silva
M.F.
, Tetrahedron Lett , 2004 , 45 , 8281 .
29.
Kabalka
G. W.
,
Zhou
L.L.
,
Wang
L.
, and
Pagni
R.M.
, Tetrahedron , 2006 , 62 , 857 .
30.
Chukhadzhyan
El.O.
,
Chukhadzhyan
E.O.
, and
Babayan
A.T.
, Zh. Org. Khim. , 1974 , 10 , 46 .
31.C.M. W, and C.J. L, , J. Am. Chem. Soc. , 2003 , 125 , 9584 .
32.
Ramu
E.
,
Varala
R.
,
Sreelatha
N.
, and
Adapa
S.R.
, Tetrahedron Lett. , 2007 , 48 , 7184 .
33.
Sreedhar
B.
,
Reddy
P.S.
,
Krishna
C.S.V.
, and
Babu
P.V.
, Tetrahedron Lett. , 2007 , 48 , 7882 .