Abstract
FeCl3·6H2O-catalysed Mizoroki–Heck reactions of aryl iodides with methyl acrylate have been achieved by using 2,2′-diamino-6,6′-dimethylbiphenyl as the ligand and NaHCO3 as the base in DMF and H2O. It was found that an appropriate amount of H2O is essential for high yields in these reactions.
References
1.
Trost B.M.
, Science , 1991 , 234 , 1471 .
2.
Tsuji J.
, Palladium reagents and catalysis: innovations in organic synthesis; Wiley : New York , 1995 .
3.
Negishi E.
, and
de Meijere A.
(eds), Handbook of organopalladium chemistry for organic synthesis , John Wiley & Sons , New York , 2002 .
4.
Heck R.F.
, J. Am. Chem. Soc. , 1968 , 90 , 5518 .
5.
de Meijere A.
, and
Meyer F.E.
, Angew. Chem. Int. Ed. Engl. , 1994 , 33 , 2379 .
6.
Cabri W.
, and
Candiani I.
, Acc. Chem. Res. , 1995 , 28 , 2 .
7.
Crisp G.T.
, Chem. Soc. Rev. , 1998 , 27 , 427 .
8.
Genet J.P.
, and
Savignac M.
, J. Organomet. Chem. , 1999 , 576 , 305 .
9.
Beletskaya I.P.
, and
Cheprakov A.V.
, Chem. Rev. , 2000 , 100 , 3009 .
10.
Amatore C.
, and
Jutand A.
, J. Organomet. Chem. , 1999 , 576 , 254 .
11.
Christmann U.
, and
Vilar R.
, Angew. Chem. Int. Ed. , 2005 , 44 , 366 .
12.
Zapf A.
, and
Beller M.
, Chem. Commun. , 2005 , 431 .
13.
Dez-González S.
, and
Nolan S.P.
, Top. Organomet. Chem. , 2007 , 21 , 47 .
14.
Beller M.
, and
Bolm C.
, Transition metals for organic synthesis , 2nd edn, Wiley : New York , 2004 , pp. 271 .
15.
Oi S.
,
Sakai K.
, and
Inoue Y.
, Org. Lett. , 2005 , 7 , 4009 .
16.
Yorke J.
,
Wan L.
,
Xia A.
, and
Zheng W.
, Tetrahedron Lett. , 2007 , 48 , 8843 .
17.
Inamoto K.
,
Kuroda J.I.
,
Hiroya K.
,
Noda Y.
,
Watanabe M.
, and
Sakamoto T.
, Organometallics , 2006 , 25 , 3095 .
18.
Yorimitsu H.
, and
Oshima K.
, Pure Appl. Chem. , 2006 , 78 , 441 .
19.
Zhou P.
,
Li Y.G.
,
Sun P.P.
,
Zhou J.H.
, and
Bao J.C.
, Chem. Commun. , 2007 , 1418 .
20.
Calò V.
,
Nacci A.
,
Monopoli A.
,
Leva E.
, and
Cioffi N.
, Org. Lett. , 2005 , 7 , 617 .
21.
Declerck V.
,
Martinez J.
, and
Lamaty F.
, Synlett , 2006 , 3029 .
22.
Cui X.
,
Li J.
,
Zhang Z.-P.
,
Fu Y.
,
Liu L.
, and
Guo Q.-X.
, J. Org. Chem. , 2007 , 72 , 9342 .
23.
Zhang X.M.
,
Xi Z.X.
,
Liu A.L.
, and
Chen W.Z.
, Organometallics , 2008 , 27 , 4401 .
24.
Monyoya V.
,
Pons J.
,
Branchadell V.
,
Garcia-Antón J.
,
Solans X.
,
Font-Bardia M.
, and
Ros J.
, Organometallics , 2008 , 27 , 1084 .
25.
Cai Y.Q.
,
Lu Y.
,
He M.Y.
, and
Wan Q.X.
, Catal. Commun. , 2008 , 9 , 1209 .
26.
Fürstner A.
, and
Martin R.
, Chem. Lett. , 2005 , 34 , 624 .
27.
Bolm C.
,
Legros J.
,
Le Paih J.
, and
Zani L.
, Chem. Rev. , 2004 , 104 , 6217 .
28.
Sherry B.D.
, and
Fürstner A.
, Acc. Chem. Res. , 2008 , 41 , 1500 .
29.
Correa A.
,
García Mancheño O.
, and
Bolm C.
, Chem. Soc. Rev. , 2008 , 37 , 1108 .
30.
Enthaler S.
,
Junge K.
, and
Beller M.
, Angew. Chem. Int. Ed. , 2008 , 47 , 3317 .
31.
Garcia Mancheno O.
, and
Bolm C.
, Iron catalysis in organic chemistry; ed.
Plietker B.
, Wiley-VCH : New York , 2008 , p. 109 .
32.
Sarhan A.A.O.
, and
Bolm C.
, Chem. Soc. Rev. , 2009 , 38 , 2730 .
33.
Bolm C.
, Nat. Chem. , 2009 , 1 , 420 .
34.
Driller K.M.
,
Klein H.
,
Jackstell R.
, and
Beller M.
, Angew. Chem. Int. Ed. , 2009 , 48 , 6041 .
35.
Fürstner A.
, Angew. Chem. Int. Ed. , 2009 , 48 , 1364 .
36.
Mao J.C.
,
Xie G.L.
,
Zhan J.M.
,
Hua Q.Q.
, and
Shi D.Q.
, Adv. Synth. Catal. , 2009 , 351 , 1268 .
37.
Xie X.
,
Xu X.B.
,
Li H.F.
,
Xu X.L.
,
Yang J.Y.
, and
Li Y.Z.
, Adv. Synth. Catal. , 2009 , 351 , 1263 .
38.
Teo Y.C.
, Adv. Synth. Catal. , 2009 , 351 , 720 .
39.
Liu W.
,
Cao H.
, and
Lei A.W.
, Angew. Chem., Int. Ed. , 2010 , 49 , 2004 .
40.
Hata T.
,
Bannai R.
,
Otsuki M.
, and
Urabe H.
, Org. Lett. , 2010 , 12 , 1012 .
41.
Maiti S.
,
Biswas S.
, and
Jana U.
, J. Org. Chem. , 2010 , 75 , 1674 .
42.
Hatakeyama T.
,
Nakagawa N.
, and
Nakamura M.
, Org. Lett. , 2009 , 11 , 4496 .
43.
Li Y.-Z.
,
Li B.-J.
,
Lu X.-Y.
,
Lin S.
, and
Shi Z.-J.
, Angew. Chem. Int. Ed. , 2009 , 48 , 3817 .
44.
Lu J.-M.
,
Ma H.
,
Li S.-S.
,
Ma D.
, and
Shao L.-X.
, Tetrahedron , 2010 , 66 , 5185 .
45.
Ye Y.-M.
,
Wang B.-B.
,
Ma D.
,
Shao L.-X.
, and
Lu J.-M.
, Cat. Lett. , 2010 , DOI: 10.1007/s10562-010-0418-9.
46.
Loska R.
,
Rao Volla C.M.
, and
Vogel P.
, Adv. Synth. Catal. , 2008 , 350 , 2859 .
47.
Ruan J.W.
,
Li X.M.
,
Saidi O.
, and
Xiao J.L.
, J. Am. Chem. Soc. , 2008 , 130 , 2424 .
48.
Yao C.F.
,
Li H.G.
,
Wu H.H.
,
Liu Y.M.
, and
Wu P.
, Catal. Commun. , 2009 , 10 , 1099 .
49.
Felpin F.X.
,
Fouquet E.
, and
Zakri C.
, Adv. Synth. Catal. , 2008 , 350 , 2559 .
50.
El-Batta A.
,
Jiang C.C.
,
Zhao W.
,
Anness R.
,
Cooksy A.L.
, and
Bergdahl M.
, J. Org. Chem. , 2007 , 72 , 5244 .