Abstract
PdCl2(1-methylimidazole)2 was an effective catalyst in neat water for the Suzuki–Miyaura and Mizoroki–Heck reactions of aryl bromides and iodides with, respectively, arylboronic acids and acrylic acid. Under optimal conditions, the products, variously substituted biphenyls and monosubstituted trans-cinnamic acids, respectively, were formed in good to almost quantitative yields.
Keywords
References
1.
Anastas
P.
, and
Warner
J.
, Green chemistry: theory and practice. Oxford University Press , New York , 1998 .
2.
Anastas
P.
, and
Eghbali
N.
, Chem. Soc. Rev. , 2012 , 39 , 301 .
3.
Butler
R.N.
, and
Coyne
A.G.
, Chem. Rev. , 2010 , 110 , 6302 .
4.
Miyaura
N.
,
Yamada
K.
, and
Suzuki
A.
, Tetrahedron Lett. , 1979 , 20 , 3437 .
5.
Miyaura
N.
, and
Suzuki
A.
, Chem. Rev. , 1995 , 95 , 2457 .
6.
Mizoroki
T.
,
Mori
K.
, and
Ozaki
A.
, Bull. Chem. Soc. Jpn , 1971 , 44 , 581 .
7.
Heck
R.F.
, and
Nolley
J.P.
Jr.
, J. Org. Chem. , 1972 , 37 , 2320 .
8.
Birkholz
M.-N.
,
Freixa
Z.
, and
van Leeuwen
P.W.N.M.
, Chem. Soc. Rev. , 2009 , 38 , 1099 .
9.
Li
J.-H.
,
Liu
W.-J.
, and
Xie
Y.-X.
, J. Org. Chem. , 2005 , 70 , 5409 .
10.
Li
J.-H.
,
Li
J.-L.
,
Wang
D.-P.
,
Pi
S.-F.
,
Xie
Y.-X.
,
Zhang
M.-B.
, and
Hu
X.-C.
, J. Org. Chem. , 2007 , 72 , 2053 .
11.
Srinivas
P.
,
Likhar
P.R.
,
Maheswaran
M.
,
Sridhar
B.
,
Ravikumar
K.
, and
Kantam
M.L.
, Chem. Eur. J. , 2009 , 15 , 1578 .
12.
Mino
T.
,
Shindo
H.
,
Kaneda
T.
,
Koizumi
T.
,
Kasashima
Y.
,
Sakamoto
M.
, and
Fujita
T.
, Tetrahedron Lett. , 2009 , 50 , 5358 .
13.
Lu
J.-M.
,
Ma
H.
,
Li
S.-S.
,
Ma
D.
, and
Shao
L.-X.
, Tetrahedron , 2010 , 66 , 5185 .
14.
Ye
Y.-M.
,
Wang
B.-B.
,
Ma
D.
,
Shao
L.-X.
, and
Lu
J.-M.
, Catal. Lett. , 2010 , 139 , 141 .
15.Palladacycles: Synthesis, characterization and applications , eds
Dupont
J.
, and
Pfeffer
M.
, Wiley-VCH : Weiheim , 2008 .
16.
Alacid
E.
,
Alonso
D.A.
,
Botella
L.
,
Nájera
C.
, and
Pacheco
M.C.
, Chem. Rec. , 2006 , 6 , 117 .
17.
Alonso
D.A.
, and
Nájera
C.
, Chem. Soc. Rev. , 2010 , 39 , 2891 .
18.
Hillier
A.C.
,
Grasa
G.A.
,
Viciu
M.S.
,
Lee
H.M.
,
Yang
C.-L.
, and
Nolan
S.P.
, J. Organomet. Chem. , 2002 , 653 , 69 .
19.
Kantchev
E.A.B.
,
O'Brien
C.J.
, and
Organ
M.G.
, Angew. Chem. Int. Ed. , 2007 , 46 , 2768 .
20.
Marion
N.
, and
Nolan
S.P.
, Acc. Chem. Res. , 2008 , 41 , 1440 .
21.
Würtz
S.
, and
Glorius
F.
, Acc. Chem. Res. , 2008 , 41 , 1523 .
22.
Fortman
G.C.
, and
Nolan
S.P.
, Chem. Soc. Rev. , 2011 , 40 , 5151 .
23.
Valente
C.
,
Çalimsiz
S.
,
Hoi
K.H.
,
Mallik
D.
,
Sayah
M.
, and
Organ
M.G.
, Angew. Chem. Int. Ed. , 2012 , 51 , 3314 .
24.
Szulmanowicz
M.S.
,
Zawartka
W.
,
Gniewek
A.
, and
Trzeciak
A.M.
, Inorg. Chim. Acta , 2010 , 363 , 4346 .
25.
Bakherad
M.
,
Keivanloo
A.
,
Bahramian
B.
, and
Jajarmi
S.
, J. Organomet. Chem. , 2013 , 724 , 206 .
26.
Ma
H.-C.
,
Cao
W.
,
Bao
Z.-K.
, and
Lei
Z.-Q.
, Catal. Sci. Technol. , 2012 , 2 , 2291 .
27.
Liu
N.
,
Liu
C.
, and
Jin
Z.-L.
, Green Chem. , 2012 , 14 , 592 .
28.
Yagyu
T.
,
Tonami
M.
,
Tsuchimoto
K.
,
Takahashi
C.
, and
Jitsukawa
K.
, Inorg. Chim. Acta , 2012 , 392 , 428 .
29.
Hong
M.C.
,
Choi
M.C.
,
Chang
Y.W.
,
Lee
Y.
,
Kim
J.
, and
Rhee
H.
, Adv. Synth. Catal. , 2012 , 354 , 1257 .
30.
Kalbasi
R.J.
,
Mosaddegh
N.
, and
Abbaspourrad
A.
, Tetrahedron Lett. , 2012 , 53 , 3763 .
31.
Tang
Y.-Q.
,
Chu
C.-Y.
,
Zhu
L.
,
Qian
B.
, and
Shao
L.-X.
, Tetrahedron , 2011 , 67 , 9479 .
32.
Ohtaka
A.
,
Tamaki
Y.
,
Igawa
Y.
,
Egami
K.
,
Shimomura
O.
, and
Nomura
R.
, Tetrahedron , 2010 , 66 , 5642 .
33.
Iranpoor
N.
,
Firouzabadi
H.
,
Tarassoli
A.
, and
Fereidoonnezhad
M.
, Tetrahedron , 2010 , 66 , 2415 .
34.
Cano
R.
,
Ramón
D.J.
, and
Yus
M.
, Tetrahedron , 2011 , 67 , 5432 .
35.
Ackermann
L.
, and
Althammer
A.
, Org. Lett. , 2006 , 8 , 3457 .
36.
Ackermann
L.
,
Kapdi
A.R.
,
Fenner
S.
,
Kornhaaß
C.
, and
Schulzke
C.
, Chem. Eur. J. , 2011 , 17 , 2965 .
37.
Leowanawat
P.
,
Zhang
N.
,
Resmerita
A.-M.
,
Rosen
B.M.
, and
Percec
V.
, J. Org. Chem. , 2011 , 76 , 9946 .
38.
Seganish
W.M.
, and
DeShong
P.
, Org. Lett. , 2004 , 6 , 4379 .
39.
Wang
Z.-Y.
,
Chen
G.-Q.
, and
Shao
L.-X.
, J. Org. Chem. , 2012 , 77 , 6608 .
40.
Saito
S.
,
Oh-tani
S.
, and
Miyaura
N.
, J. Org. Chem. , 1997 , 62 , 8024 .
41.
Jothibasu
R.
,
Huang
K.-W.
, and
Huynh
H.V.
, Organometallics , 2010 , 29 , 3746 .
42.
Zhou
W.-J.
,
Wang
K.-H.
,
Wang
J.-X.
, and
Gao
Z.-R.
, Tetrahedron , 2010 , 66 , 7633 .
43.
Zhang
J.-L.
,
Zhao
L.
,
Song
M.-P.
,
Mak
T.C.W.
, and
Wu
Y.-J.
, J. Organomet. Chem. , 2006 , 691 , 1301 .
44.
Liang
L.-C.
,
Chien
P.-S.
, and
Huang
M.-H.
, Organometallics , 2005 , 24 , 353 .
45.
Fukuyama
T.
,
Arai
M.
,
Matsubara
H.
, and
Ryu
I.
, J. Org. Chem. , 2004 , 69 , 8105 .
46.
Peterson
J.R.
,
Russell
M.E.
, and
Surjasasmlta
I.B.
, J. Chem. Eng. Data , 1988 , 33 , 534 .
47.
Artuso
E.
,
Barbero
M.
,
Degani
I.
,
Dughera
S.
, and
Fochi
R.
, Tetrahedron , 2006 , 62 , 3146 .
