Abstract
The Heck arylation reaction of aryl iodides with allylic alcohols catalysed by an mesoporous silica (MCM-41)-supported bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2] proceeded smoothly in the presence of tetrabutylammonium chloride (TBAC) in DMF to afford β-aryl ketones in good to excellent yields. This heterogeneous palladium catalyst can be recovered by simple filtration and reused several times without any decrease in activity.
Keywords
References
1.
Dearden J.C.
, and
Nicholson R.M.
, J. Pharm. Pharmacol. , 1984 , 36 , 713 .
2.
Ducki S.
,
Hadfield J.A.
,
Hepworth L.A.
,
Lawrence N.J.
,
Liu C.-Y.
, and
McGown A.T.
, Bioorg. Med. Chem. Lett. , 1997 , 7 , 3091 .
3.
Murthy Y.V.S.N.
,
Meah Y.
, and
Massey V.
, J. Am. Chem. Soc. , 1999 , 121 , 5344 .
4.
Liao Y.-X.
,
Xing C.-H.
,
Israel M.
, and
Hu Q.-S.
, Org. Lett. , 2011 , 13 , 2058 .
5.
Melpolder J.B.
, and
Heck R.F.
, J. Org. Chem. , 1976 , 41 , 265 .
6.
Chalk A.J.
, and
Magennis S.A.
, J. Org. Chem. , 1976 , 41 , 273 .
7.
Smadja W.
,
Czernecki S.
,
Ville G.
, and
Georgoulis C.
, Organometallics , 1987 , 6 , 166 .
8.
Basavaiah D.
, and
Muthukumaran K.
, Tetrahedron , 1998 , 54 , 4943 .
9.
Bouquillon S.
,
Ganchegui B.
,
Estrine B.
,
Henin F.
, and
Muzart J.
, J. Organomet. Chem. , 2001 , 634 , 153 .
10.
Bagnell L.
,
Kreher U.
, and
Strauss C.R.
, Chem. Commun. , 2001 , 29 .
11.
Beletskaya I.P.
, and
Cheprakov A.V.
, Chem. Rev. , 2000 , 100 , 3009 .
12.
Jeffery T.J.
, J. Chem. Soc., Chem. Commun. , 1991 , 324 .
13.
Kang S.-K.
,
Lee H.-W.
,
Jiang S.-B.
,
Kim T.-H.
, and
Pyun S.-J.
, J. Org. Chem. , 1996 , 61 , 2604 .
14.
Calo V.
,
Nacci A.
,
Monopoli A.
, and
Spinelli M.
, Eur. J. Org. Chem. , 2003 , 1382 .
15.
Fan Q.
,
Li X.
, and
Chan A.S.C.
, Chem. Rev. , 2002 , 102 , 3385 .
16.
Song C.E.
, Chem. Commun. , 2004 , 1033 .
17.
Poliakoff M.
,
Fitzpatrick J.M.
,
Farren T.R.
, and
Anastas P.T.
, Science , 2002 , 297 , 807 .
18.
Kirschnig A.
,
Monenschein H.
, and
Wittenberg R.
, Angew. Chem., Int. Ed. , 2001 , 40 , 650 .
19.
Clapham B.
,
Reger T.S.
, and
Janda K.D.
, Tetrahedron , 2001 , 57 , 4637 .
20.
Leadbeater N.E.
, and
Marco M.
, Chem. Rev. , 2002 , 102 , 3217 .
21.
Yin L.
, and
Liebscher J.
, Chem. Rev. , 2007 , 107 , 133 .
22.
Wang P.-W.
, and
Fox M.A.
, J. Org. Chem. , 1994 , 59 , 5358 .
23.
Cai M.-Z.
,
Song C.-S.
, and
Huang X.
, Synthesis , 1997 , 521 .
24.
Khan S.I.
, and
Grinstaff M.W.
, J. Org. Chem. , 1999 , 64 , 1077 .
25.
Yu K.
,
Sommer W.
,
Richardson J.M.
,
Week M.
, and
Jones C.W.
, Adv. Synth. Catal. , 2005 , 347 , 161 .
26.
Clark J.H.
,
Macquarrie D.J.
, and
Mubofu E.B.
, Green Chem. , 2000 , 2 , 53 .
27.
Kresge C.T.
,
Leonowicz M.E.
,
Roth W.J.
,
Vartuli J.C.
, and
Beck J.S.
, Nature , 1992 , 359 , 710 .
28.
Beck J.S.
,
Vartuli J.C.
,
Roth W.J.
,
Leonowicz M.E.
,
Kresge C.T.
,
Schmitt K.D.
,
Chu C.T.-W.
,
Olson D.H.
,
Sheppard E.W.
,
McCullen S.B.
,
Higgins J.B.
, and
Schlenker J.L.
, J. Am. Chem. Soc. , 1992 , 114 , 10834 .
29.
Zhou W.
,
Thomas J.M.
,
Shephard D.S.
,
Johnson B.F.G.
,
Ozkaya D.
,
Maschmeyer T.
,
Bell R.G.
, and
Ge Q.
, Science , 1998 , 280 , 705 .
30.
Maschmeyer T.
,
Rey F.
,
Sankar G.
, and
Thomas J.M.
, Nature , 1995 , 378 , 159 .
31.
Liu C.-J.
,
Li S.-G.
,
Pang W.-Q.
, and
Che C.-M.
, Chem. Commun. , 1997 , 65 .
32.
Mehnert P.C.
,
Weaver D.W.
, and
Ying J.Y.
, J. Am. Chem. Soc. , 1998 , 120 , 12289 .
33.
Yang H.
,
Zhang G.
,
Hong X.
, and
Zhu Y.
, J. Mol. Catal. A: Chem. , 2004 , 210 , 143 .
34.
Gonzalez-Arellano C.
,
Corma A.
,
Iglesias M.
, and
Sanchez F.
, Adv. Synth. Catal. , 2004 , 346 , 1758 .
35.
Alonso F.
,
Beletskaya I.P.
, and
Yus M.
, Tetrahedron , 2005 , 61 , 11771 .
36.
Lempers H.E.B.
, and
Sheldon R.A.
, J. Catal. , 1998 , 175 , 62 .
37.
Lim M.H.
, and
Stein A.
, Chem. Mater. , 1999 , 11 , 3285 .