Abstract
A palladium catalyst supported on a Merrifield resin was prepared by a simple procedure and exhibited high activity and stability for the phosphine-free Heck reaction of activated and non-activated aryl or heteroaryl substrates with olefins to afford substituted cinnamic acids, stilbenes and their hetero-aromatic relatives.
References
1.
Heck R.F.
, Acc. Chem. Res. , 1979 , 12 , 146 .
2.
Beletskaya I.P.
, and
Cheprakov A.V.
, Chem. Rev. , 2000 , 100 , 3009 .
3.
Whitcombe N.J.
,
Hii K.K.M.
, and
Gibson S.E.
, Tetrahedron. , 2001 , 57 , 7449 .
4.
Hallberg A.
, and
Westfelt L.
, J. Chem. Soc. Perkin Trans. 1. , 1984 , 933 .
5.
Zhao F.Y.
,
Bhanage B.M.
,
Shirai M.
, and
Arai M.
, Chem. Eur. J. , 2000 , 6 , 843
6.
Djakovitch L.
, and
Koehler K.
, J. Mol. Catal. A. , 1999 , 142 , 275
7.
Djakovitch L.
, and
Koehler K.
, J. Am. Chem. Soc. , 2001 , 123 , 5990
8.
Mehnert C.P.
,
Weaver D.W.
, and
Ying J.Y.
, J. Am. Chem. Soc. , 1998 , 120 , 12289
9.
Augustine R.L.
, and
O'Leary S.T.
, J. Mol. Catal. A. , 1995 , 95 , 277 .
10.
Andersson C.M.
,
Karabelas K.
,
Hallberg A.
, and
Andersson C.
, J. Org. Chem. , 1985 , 50 , 3891 .
11.
Dahan A.
, and
Portnoy M.
, Org. Lett. , 2003 , 5 , 1197 .
12.
Uozumi Y.
, and
Kimura T.
, Synlett. , 2002 , 12 , 2045 .
13.
Nowotny M.
,
Hanefeld U.
,
van Koningsveld H.
, and
Maschmeyer T.
, Chem. Commun. , 2000 , 1877 .
14.
Buchmeiser M.R.
, and
Wurst K.
, J. Am. Chem. Soc. , 1999 , 121 , 11101 .
15.
Chandrasekhar V.
, and
Athimoolam A.
, Org. Lett. , 2002 , 4 , 2113 .
16.
Schwarz J.
,
Böhm V.P.W.
,
Gardiner M.G.
,
Grosche M.
,
Herrmann W.A.
,
Hieringer W.
, and
Raudaschl-Sieber G.
, Chem. Eur. J. , 2000 , 6 , 1773 .
17.
Bräse S.
, and
Schroen M.
, Angew. Chem. Int. Ed. , 1999 , 38 , 1071 .
18.
Jeffery T.
Tetrahedron. , 1996 , 52 , 10113 .
19.
Jeffery T.
, and
David M.
, Tetrahedron Lett. , 1998 , 39 , 5751 .
20.
Aksýn Ö.
,
Türkmen H.
, and
Artok L.
, J. Organomet. Chem. , 2006 , 691 , 3027 .
21.
Cui X.
,
Li Z.
, and
Tao C.Z.
, Org. Lett. , 2006 , 8 , 2467 .
22.
Cwik A.
,
Hell Z.
, and
Figueras F.
, Adv. Synth. Catal. , 2006 , 348 , 523 .
23.
Zhang Z.H.
,
Zha Z.G.
, and
Gan C.S.
, J. Org. Chem. , 2006 , 71 , 4339 .
24.
Myers A.G.
,
Tanaka D.
, and
Mannion M.R.
, J. Am. Chem. Soc. , 2002 , 124 , 11250 .
25.
Dai M.J.
,
Liang B.
,
Wang C.H.
,
Chen J.H.
, and
Yang Z.
, Org. Lett. , 2004 , 6 , 221 .
26.
Feuerstein M.
,
Doucet H.
, and
Santelli M.
, J. Org. Chem. , 2001 , 66 , 5923 .
27.
Berthiol F.
,
Feuerstein M.
,
Doucet H.
, and
Santelli M.
, Tetrahedron Lett. , 2002 , 43 , 5625 .