Abstract
A simple economical, and highly efficient catalytic system for the synthesis of diaryl sulfides by a copper-catalysed coupling of aryl halides and thioacetate in water has been developed. A variety of aryl halides reacted with thioacetate to give the desired products in high yields up to 95%. The present catalysis protocol tolerated a wide range of functional groups, including amino, fluoro, and carboxyl moieties.
References
1.
Jones
D.N.
, Comprehensive organic chemistry ,
Barton
D.H.
, and
Ollis
D.W.
, eds. Pergamon , New York , 1979 , Vol. 3 .
2.
Tiecco
M.
, Synthesis , 1988 , 749 .
3.
Hassan
J.
,
Sevignon
M.
,
Gozzi
C.
,
Schulz
E.
, and
Lemaire
M.
, Chem. Rev. , 2002 , 102 , 1359 .
4.
Beletskaya
I.P.
, and
Cheprakov
A.V.
, Coord. Chem. Rev. , 2004 , 248 , 2337 .
5.
Ley
S.V.
, and
Thoma
A.W.
, Angew. Chem. Int. Ed. , 2003 , 42 , 5400 .
6.
Herradura
P.S.
,
Pendola
K.A.
, and
Guy
R.K.
, Org. Lett. , 2000 , 2 , 2019 .
7.
Procter
D.J.
, J. Chem. Soc. Perkin Trans., 1 2001 , 335 .
8.
Lindley
J.
, Tetrahedron , 1984 , 40 , 1433 .
9.
Bordwell
F.G.
, and
McKellin
W.H.
, J. Am. Chem. Soc. , 1951 , 73 , 2251 .
10.
Migita
T.
,
Shimisu
T.
,
Asami
Y.
,
Shiobara
J.
,
Kato
Y.
, and
Kosugi
M.
, Bull. Chem. Soc. Jpn. , 1980 , 53 , 1385
11.
Li
G.
, Angew. Chem. Int. Ed. , 2001 , 40 , 1513 .
12.
Murata
M.
, and
Buchwald
S.L.
, Tetrahedron , 2004 , 60 , 7397 .
13.
Fernández-Rodríguez
M.A.
,
Shen
Q.
, and
Hartwig
J.F.
, Chem. Eur. J. , 2006 , 12 , 7782 .
14.
Itoh
T.
, and
Mase
T.
, Org. Lett. , 2004 , 6 , 4587 .
15.
Zhang
Y.
,
Ngeow
K.N.
, and
Ying
J.
, Org. Lett. , 2007 , 9 , 3495 .
16.
Jammi
S.
,
Barua
P.
,
Rout
L.
,
Saha
P.
, and
Punniyamurthy
T.
, Tetrahedron Lett. , 2008 , 49 , 1484 .
17.
Wong
Y.
,
Jayanth
T.T.
, and
Cheng
C.
, Org. Lett. , 2006 , 8 , 5613 .
18.
Reddy
V.P.
,
Swapna
K.
,
Kumar
A.V.
, and
Rao
K.
, J. Org. Chem. , 2009 , 74 , 3189 .
19.
Reddy
V.P.
,
Kumar
A.V.
,
Swapna
K.
, and
Rao
K.
, Org. Lett. , 2009 , 11 , 1697 .
20.
Murthy
S.N.
,
Madhav
B.
,
Reddy
V.P.
,
Durga–Nageswar
Y.V.
, Eur. J. Org. Chem. , 2009 , 5902 .
21.
Correa
A.
,
Carril
M.
, and
Bolm
C.
, Angew. Chem. Int. Ed. , 2008 , 47 , 2880 .
22.
Wu
W.
,
Wang
J.
, and
Tsai
F.Y.
, Green. Chem. , 2009 , 11 , 326 .
23.
Ley
S.V.
, and
Thomas
A.W.
, Angew. Chem. Int. Ed. , 2003 , 42 , 5400 .
24.
Beletskaya
I.P.
, and
Cheprakov
A.V.
, Coord. Chem. Rev. , 2004 , 248 , 2337 .
25.
Firouzabadi
H.
,
Iranpoor
N.
, and
Gholinejad
M.
, Adv. Synth. Catal. , 2010 , 352 , 119 .
26.
Ke
F.
,
Qu
Y.
,
Jiang
Z.
,
Li
Z.
,
Wu
D.
, and
Zhou
X.
, Org. Lett. , 2011 , 13 , 454 .
27.
Zhang
S.
,
Qian
P.
,
Zhang
M.
,
Hu
M.
, and
Cheng
J.
, J. Org. Chem. , 2010 , 75 , 6732 .
28.
Ma
D.
,
Xie
S.
,
Xue
P.
,
Zhang
X.
,
Dong
J.
,
Jiang
Y.
, Angew. Chem. Int. Ed. , 2009 , 48 , 4222 .
29.
You
W.
,
Yan
X.
,
Liao
Q.
, and
Xi
C.
, Org. Lett. , 2010 , 12 , 3930 .
30.
Lai
C.
, and
Backes
B.J.
, Tetrahedron Lett. , 2007 , 48 , 3033 .
31.
Park
N.
,
Park
K.
,
Jang
M.
, and
Lee
S.
, J. Org. Chem. , 2011 , 76 , 4371 .
32.
Narayan
S.
,
Muldoon
J.
,
Finn
M.G.
,
Fokin
V.V.
,
Kolb
H.C.
, and
Sharpless
K.B.
, Angew. Chem., Int. Ed. , 2005 , 44 , 3275 .
33.
Li
C.
, Chem. Rev. , 2005 , 105 , 3095 .
34.
Dallinger
D.
, and
Kappe
C.O.
, Chem. Rev. , 2007 , 107 , 2563 .
35.
Chanda
A.
, and
Fokin
V.V.
, Chem. Rev. , 2009 , 109 , 725 .
36.
Chen
J.
,
Yuan
T.
,
Hao
W.
, and
Cai
M.
, Tetrahedron Lett. , 2011 , 52 , 3710 .
37.
Chen
J.
,
Yuan
T.
,
Hao
W.
, and
Cai
M.
, Catal. Commun. , 2011 , 12 , 1463 .
38.
Hauptmann
H.
,
Walter
W.
,
Marino
C.
, J. Am. Chem. Soc. , 1958 , 80 , 5832 .
39.
Clark
J.H.
,
Jones
C.W.
,
Duke
C.V.A.
, and
Miller
J.M.
, J. Chem. Soc. Chem. Commun. 1989 , 81 .
40.
Artemèva
V.N.
,
Chupans
P.I.
,
Kukarkina
N.V.
,
Fedorova
G.N.
,
Sazanov
Y.N.
,
Denisov
V.M.
, and
Kudryavtsev
V.V.
, Russ. J. Appl. Chem. , 2000 , 73 , 860 .
41.
García
N.
,
García-García
P.
,
Fernández-Rodríguez
M.A.
,
Rubio
R.
,
Pedrosa
M.R.
,
Arnáiz
F.J.
, and
Sanz
R.
, Adv. Synth. Catal. , 2012 , 354 , 321 .
42.
Du
X.
,
Liu
H.
, and
Du
D.
, Tetrahedron: Asymmetry , 2010 , 21 , 241 .
43.
Montaudo
G.
,
Finocchiaro
P.
,
Trivellone
E.
,
Bottin
F.
, and
Maravigna
P.
, Tetrahedron , 1971 , 27 , 2125 .
44.
Sadorn
K.
,
Sinananwanich
W.
,
Areephong
J.
,
Nerungs
C.
,
Wongma
C.
,
Pakawatchai
C.
, and
Thongpanchang
T.
, Tetrahedron Let. , 2008 , 49 , 4519 .
