Abstract
Palladium acetate-catalysed Suzuki reaction of halopyridines and arylboronic acids has been investigated in room-temperature ionic liquids in the absence of the phosphine ligand. A significant effect of water on the efficiency of the Suzuki reaction in ionic liquids was observed. The mixture of ionic liquid and water significantly enhanced the rate of the coupling reaction. The separation of the product was easily performed by extraction with diethyl ether and the Pd(OAc)2–[bmim][PF6] (1-butyl-3-methylimidazolium hexafluorophosphate) can be reused six times with only a small loss of reactivity.
References
1.
Hassan
J.
,
Sevignon
M.
,
Gozzi
C.
,
Schulz
E.
, and
Lemaire
M.
, Chem. Rev. , 2002 , 102 , 1359 .
2.
Yin
L.X.
, and
Liebscher
J.
, Chem. Rev. , 2007 , 107 , 133 .
3.
Miyaura
N.
, and
Suzuki
A.
, Chem. Rev , 1995 , 95 , 2457 .
4.
Baudoin
O.
,
Cesario
M.
,
Guenard
D.
, and
Gueritte
F.
, J. Org. Chem. , 2002 , 67 , 1199 .
5.
Wong
K.T.
,
Hung
T.S.
,
Lin
Y.
,
Wu
C.C.
,
Lee
G.H.
,
Peng
S.M.
,
Chou
C.H.
, and
Su
Y.O.
, Org. Lett , 2002 , 4 , 513 .
6.
Kotha
S.
,
Lahiri
K.
, and
Kashinath
D.
, Tetrahedron , 2002 , 58 , 9633 .
7.
Nicolaou
K.C.
,
Boddy
C.N.C.
,
Brase
S.
, and
Winssinger
N.
, Angew. Chem., Int. Ed. , 1999 , 38 , 2096 .
8.
Handy
S.T.
,
Wilson
T.
, and
Muth
A.
, J. Org. Chem. , 2007 , 72 , 8496 .
9.
Guram
A.S.
,
Wang
X.
,
Bunel
E.E.
,
Faul
M.M.
,
Larsen
R.D.
, and
Martinelli
M.J.
, J. Org. Chem. , 2007 , 72 , 5104 .
10.
Savarin
C.
, and
Liebeskind
L.S.
, Org. Lett. , 2001 , 3 , 2149 .
11.
Wolfe
J.P.
,
Singer
R.A.
,
Yang
B.H.
, and
Buchwald
S.L.
, J. Am. Chem. Soc. , 1999 , 121 , 9550 .
12.
Mori
K.
,
Yamaguchi
K.
,
Hara
T.
,
Mizugaki
T.
,
Ebitani
K.
, and
Kaneda
K.
, J. Am. Chem. Soc. , 2002 , 124 , 11572 .
13.
Botella
L.
, and
Najera
C.
, Angew. Chem. Int. Ed , 2002 , 41 , 179 .
14.
Lohse
O.
,
Thevenin
P.
, and
Waldvogel
E.
, Synlett , 1999 , 1 , 45 .
15.
Gong
Y.
, and
Pauls
H.W.
, Synlett , 2000 , 6 , 829 .
16.
Tagata
T.
, and
Nishida
M.
, J. Org. Chem. , 2003 , 68 , 9412 .
17.
Dupont
J.
,
de Souza
R.F.
, and
Suarez
P.A.
, Z. Chem. Rev. , 2002 , 102 , 3667 .
18.
Welton
T.
, Chem. Rev , 1999 , 99 , 2071 .
19.
Tzschucke
C.C.
,
Markert
C.
,
Bannwarth
W.
,
Roller
S.
,
Hebel
A.
, and
Haag
R.
, Angew. Chem. Int. Ed. , 2002 , 41 , 3964 .
20.
Earle
M.J.
, and
Seddon
K.R.
, Pure Appl. Chem. , 2000 , 72 , 1391 .
21.
Swatloski
R.P.
,
Visser
A.E.
,
Reichert
W.M.
,
Broker
G.A.
,
Farina
L.M.
,
Holbrey
J.D.
, and
Rogers
R.D.
, Chem. Commun. , 2001 , 2070 .
22.
Xin
B.W.
,
Zhang
Y.H.
, and
Cheng
K.
, J. Org. Chem. , 2006 , 71 , 5725 .
23.
Xin
B.W.
,
Zhang
Y.H.
,
Liu
L.F.
, and
Wang
Y.G.
, Synlett , 2005 , 20 , 3083 .
24.
Feuerstein
M.
,
Doucet
H.
, and
Santelli
M.
, Tetrahedron Lett , 2001 , 42 , 5659 .
25.
Mathews
C.J.
,
Smith
P.J.
,
Welton
T.
,
White
A.J.P.
, and
Williams
D.J.
, Organometallics , 2001 , 20 , 3848 .
26.
Gordillo
A.
, and
Jesús
E.
,
López-Mardomingo
C.
, Org. Lett. , 2006 , 8 , 3517 .
27.
Le Notre
J.
,
Firet
J.J.
,
Sliedregt
L.A.J.M.
,
van Steen
B.J.
,
van Koten
G.
, and
Klein Gebbink
R.J.M.
, Org. Lett. , 2005 , 7 , 363 .
28.
US Patent 6399656.
29.
Saris
C.P.
,
Van Dijk
W.J.
,
Westra
J.G.
,
Hamzink
M.R.
,
van de Werken
G.
,
Zomer
G.
, and
Stavenuiter
J.F.
, Chem Biol Interact , 1995 , 95 (1–2 ), 29 .
30.
Adjabeng
G.
,
Brenstrum
T.
,
Wilson
J.
,
Frampton
C.
,
Robertson
A.
,
Hillhouse
J.
,
McNulty
J.
, and
Capretta
A.
, Org. Lett. , 2003 , 5 , 953 .
31.
US Patent 6096894.