Abstract
Three inexpensive and air-/moisture-stable complexes (Salden)Cu (Salden = N, N’-bis(salicylidene)-1,2-dimethylethylenediamine), (Saldch)Cu (Saldch = N, N’-bis(salicylidene)-1,2-cyclohexenediamine), and (Salph)Cu (salph = N, N’-bis(salicylidene)-1,2-phenylenediamine) were synthesised and evaluated as catalysts for the N-arylation of pyrazole with aryl halides. A variety of aryl iodides and bromides underwent coupling with pyrazole, promoted by the (Saldch)Cu complex, in moderate to excellent yields without the protection by an inert gas.
References
1.
Elguero J.
, Comprehensive heterocyclic chemistry II , 1st edn, Vol. 3 , eds
Katritzky A.R.
,
Rees C.W.
, and
Scriven E.F.V.
, Pergamon, Elsevier , Oxford , 1996 , p. 70 .
2.
Lam P.Y.S.
,
Vincent G.
,
Clark C.G.
,
Deudon S.
, and
Jadhav P.K.
, Tetrahedron Lett. , 2001 , 42 , 3415 .
3.
Lopez-Alvarado P.
,
Avendano C.
, and
Menendez J.C.
, J. Org. Chem. , 1995 , 60 , 5678 .
4.
Lam P.Y.S.
,
Clark C.G.
,
Saubern S.
,
Adams J.
,
Verill K.M.
,
Chan D.M.T.
, and
Combs A.
, Synlett , 2000 , 674 .
5.
Finet J.-P.
, and
Fedorov A.Y.
, Tetrahedron Lett. , 1999 , 40 , 2747 .
6.
Kang S.-K.
,
Lee S.-H.
, and
Lee D.
, Synlett , 2000 , 1022 .
7.
Klapars A.
,
Antilla J.C.
,
Huang X.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2001 , 123 , 7727 .
8.
Liu P.
,
Feng X.-J.
, and
He R.
, Tetrahedron , 2010 , 66 , 631 .
9.
Wang Y.
,
Wu Z.Q.
,
Wang L.X.
,
Li Z.K.
, and
Zhou X.G.
, Chem. Eur. J. , 2009 , 15 , 8971 .
10.
Wu Z.Q.
,
Zhou L.
,
Jiang Z.Q.
,
Wu D.
,
Li Z.K.
, and
Zhou X.G.
, Eur. J. Org. Chem. , 2010 , 4971 .
11.
Wu Z.Q.
,
Jiang Z.Q.
,
Wu D.
,
Xiang H.F.
, and
Zhou X.G.
, Eur. J. Org. Chem. , 2010 , 1854 .
12.
Giricheva N.I.
,
Girichev G.V.
,
Kuzmina N.P.
,
Medvedeva Y.S.
, and
Rogachev A.Y.
, J. Struct. Chem. 50 , 52 .
13.
Belokon Y.N.
,
Davies R.G.
,
Fuentes J.A.
,
North M.
, Tetrahedron Lett. , 2001 , 42 , 8093 .
14.
Correa A.
, and
Bolm C.
, Angew. Chem. Int. Ed. , 2007 , 46 , 8862 .
15.
Cristau H.-J.
,
Cellier P. P.
,
Spindler J.-F.
, and
Taillefer M.
, Eur. J. Org. Chem. , 2004 , 695 .
16.
Khan M.A.
,
Lynch B.M.
, and
Hung Y.-Y.
, Can. J. Chem. , 1963 , 41 , 1540 .