Abstract
The heterogeneous O-arylation of phenols by nitroarenes was achieved in DMF at 100 °C by using an MCM-41-immobilised bidentate nitrogen copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst, yielding a variety of unsymmetrical diaryl ethers in good to excellent yields. This heterogeneous copper catalyst can be easily prepared by a simple procedure from commercially readily available and inexpensive reagents, recovered by filtration of the reaction solution and recycled at least seven times without significant loss of activity.
References
1.
Nicolaou K.C.
,
Boddy C.N.C.
,
Brase S.
, and
Winssinger N.
, Angew. Chem., Int. Ed. , 1999 , 38 , 2096 .
2.
Pulman D.A.
, J. Agric. Food Chem. , 2011 , 59 , 2770 .
3.
Strukelj M.
,
Papadimitrakopoulos F.
,
Miller T.M.
, and
Rothberg L.J.
, Science , 1995 , 267 , 1969 .
4.
Monnier F.
, and
Taillefer M.
, Angew. Chem., Int. Ed. , 2009 , 48 , 6954 .
5.
Ullmann F.
, Ber. Dtsch. Chem. Ges. , 1904 , 37 , 853 .
6.
Lindley J.
, Tetrahedron , 1984 , 40 , 1433 .
7.
Evano G.
,
Blanchard N.
, and
Toumi M.
, Chem. Rev. , 2008 , 108 , 3054 .
8.
Mann G.
, and
Hartwig J.F.
, J. Org. Chem. , 1997 , 62 , 5413 .
9.
Mann G.
,
Incarvito C.
,
Rheingold A.L.
, and
Hartwig J.F.
, J. Am. Chem. Soc. , 1999 , 121 , 3224 .
10.
Aranyos A.
,
Old D.W.
,
Kiyomori A.
,
Wolfe J.P.
,
Sadighi J.P.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 1999 , 121 , 4369 .
11.
Burgos C.H.
,
Barder T.E.
,
Huang X.
, and
Buchwald S.L.
, Angew. Chem., Int. Ed. , 2006 , 45 , 4321 .
12.
Hu T.
,
Schulz T.
,
Torborg C.
,
Chen X.
,
Wang J.
,
Beller M.
, and
Huang J.
, Chem. Commun. , 2009 , 7330 .
13.
Marcoux J.-F.
,
Doye S.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 1997 , 119 , 10539 .
14.
Buck E.
,
Song Z.J.
,
Tschaen D.
,
Dormer P.G.
,
Volante R.P.
, and
Reider P.J.
, Org. Lett. , 2002 , 4 , 1623 .
15.
Cai Q.
,
Zou B.
, and
Ma D.
, Angew. Chem., Int. Ed. , 2006 , 45 , 1276 .
16.
Monnier F.
, and
Taillefer M.
, Angew. Chem., Int. Ed. , 2009 , 48 , 6954 .
17.
Fan M.
,
Zhou W.
,
Jiang Y.
, and
Ma D.
, Angew. Chem., Int. Ed. , 2016 , 55 , 6211 .
18.
Evans D.A.
,
Katz J.L.
, and
West T.R.
, Tetrahedron Lett. , 1998 , 39 , 2937 .
19.
Decicco C.P.
,
Song S.
, and
Evans D.A.
, Org. Lett. , 2001 , 3 , 1029 .
20.
Lam P.Y.S.
,
Vincent G.
,
Clark C.
,
Deudon S.
, and
Jadhav P.K.
, Tetrahedron Lett. , 2001 , 42 , 3415 .
21.
Qiao J.X.
, and
Lam P.Y.S.
, Synthesis , 2011 , 829 .
22.
Zhang J.
,
Chen J.
,
Liu M.
,
Zheng X.
,
Ding J.
, and
Wu H.
, Green Chem. , 2012 , 14 , 912 .
23.
Chen J.
,
Wang X.
,
Zheng X.
,
Ding J.
,
Liu M.
, and
Wu H.
, Tetrahedron , 2012 , 68 , 8905 .
24.
Takise R.
,
Isshiki R.
,
Muto K.
,
Itami K.
, and
Yamaguchi J.
, J. Am. Chem. Soc. , 2017 , 139 , 3340 .
25.
Wang L.
,
Zhang J.
,
Sun J.
,
Zhu L.
,
Zhang H.
,
Liu F.
,
Zheng D.
,
Meng X.
,
Shi X.
, and
Xiao F.-S.
, ChemCatChem , 2013 , 5 , 1606 .
26.
Zhai Z.
,
Guo X.
,
Jiao Z.
,
Jin G.
, and
Guo X.-Y.
, Catal. Sci. Technol. , 2014 , 4 , 4196 .
27.
Benyahya S.
,
Monnier F.
,
Taillefer M.
,
Man M.W.C.
,
Bied C.
, and
Ouazzani F.
, Adv. Synth. Catal. , 2008 , 350 , 2205 .
28.
Benyahya S.
,
Monnier F.
,
Man M.W.C.
,
Bied C.
,
Ouazzani F.
, and
Taillefer M.
, Green Chem. , 2009 , 11 , 1121 .
29.
Magne V.
,
Garnier T.
,
Danel M.
,
Pale P.
, and
Chassaing S.
, Org. Lett. , 2015 , 17 , 4494 .
30.
Kresge C.T.
,
Leonowicz M.E.
,
Roth W.J.
,
Vartuli J.C.
, and
Beck J.S.
, Nature , 1992 , 359 , 710 .
31.
Xiao R.
,
Yao R.
, and
Cai M.
, Eur. J. Org. Chem. , 2012 , 4178 .
32.
Xiao R.
,
Zhao H.
, and
Cai M.
, Tetrahedron , 2013 , 69 , 5444 .
33.
Zhao H.
,
He W.
,
Yao R.
, and
Cai M.
, Adv. Synth. Catal. , 2014 , 356 , 3092 .
34.
Cai M.
,
Yao R.
,
Chen L.
, and
Zhao H.
, J. Mol. Catal. A: Chem. , 2014 , 395 , 349 .
35.
Zhao H.
,
Jiang Y.
,
Chen Q.
, and
Cai M.
, New J. Chem. , 2015 , 39 , 2106 .
36.
Zhao H.
,
He W.
,
Wei L.
, and
Cai M.
, Catal. Sci. Technol. , 2016 , 6 , 1488 .
37.
Lempers H.E.B.
, and
Sheldon R.A.
, J. Catal. , 1998 , 175 , 62 .
38.
Jepsen T.H.
,
Larsen M.
,
Jorgensen M.
, and
Nielsen M.B.
, Synlett , 2012 , 418 .
39.
Yang S.
,
Wu C.
,
Ruan M.
,
Yang Y.
,
Zhao Y.
,
Niu J.
,
Yang W.
, and
Xu J.
, Tetrahedron Lett. , 2012 , 53 , 4288 .
40.
Comeau A.B.
,
Critton D.A.
,
Page R.
, and
Seto C.T.
, J. Med. Chem. , 2010 , 53 , 6768 .