Abstract
A simple, inexpensive and ligand-free copper-catalysed N-arylation of pyrrole with aryl iodides has been developed giving N-arylated products in moderate to excellent yields. The catalyst loading is relative low (5 mol%) and the catalyst system was stable in air.
References
1.
Sawant P.
, and
Maier M.E.
, Tetrahedron , 2010 , 66 , 9738 .
2.
Gupta R.R.
,
Kumar M.
, and
Gupta V.
, Heterocyclic chemistry II: five-membered heterocycles. Springer , Berlin , 1999 .
3.
Banik M.
,
Ramirez B.
,
Reddy A.
,
Bandyopadhyay D.
, and
Banik B.K.
, Org. Med. Chem. Lett. , 2012 , 2 , 11 .
4.
Li Z.
,
Wu Z.
,
Deng H.
, and
Zhou X.
, Chin. J. Org. Chem. , 2013 , 33 , 760 (in Chinese).
5.
Monnier F.
, and
Taillefer M.
, Angew. Chem. Int. Ed. , 2009 , 48 , 6954 .
6.
Senra J.D.
,
Aguiar L.C.S.
, and
Simas A.B.C.
, Curr. Org. Synth. , 2011 , 8 , 53 .
7.
Monnier F.
, and
Taillefer M.
, Angew. Chem. Int. Ed. , 2008 , 47 , 3096 .
8.
Wang Y.
,
Zeng J.
, and
Cui X.
, Chin. J. Org. Chem. , 2010 , 30 , 181 (in Chinese).
9.
Chang J.W.W.
,
Xu X.
, and
Chan P.W.H.
, Tetrahedron Lett. , 2007 , 48 , 245 .
10.
Yang Q.
,
Wang Y.
,
Zhang B.
, and
Zhang M.
, Chin. J. Chem. , 2012 , 30 , 2389 .
11.
Zhu R.
,
Xing L.
,
Wang X.
,
Cheng C.
,
Su D.
, and
Hu Y.
, Adv. Synth. Catal. , 2008 , 350 , 1253 .
12.
Correa A.
, and
Bolm C.
, Adv. Synth. Catal. , 2007 , 349 , 2673 .
13.
Jiao Y.
,
Yan N.
,
Xie J.
,
Ma X.
,
Liu P.
, and
Dai B.
, Chin. J. Chem. , 2013 , 31 , 267 .
14.
Wu F.-T.
,
Liu P.
,
Ma X.-W.
,
Xie J.-W.
, and
Dai B.
, Chin. Chem. Lett. , 2013 , 24 , 893 .
15.
Liu Y.
,
Liu W.
,
Zhang Q.
,
Liu P.
,
Xie J.-W.
, and
Dai B.
, J. Chem. Res. , 2013 , 37 , 636 .
16.
Ma F.-P.
,
Li P.-H.
,
Li B.-L.
,
Mo L.-P.
,
Liu N.
,
Kang H.-J.
,
Liu Y.-N.
, and
Zhang Z.-H.
, Appl. Catal. A: Gen. , 2013 , 457 , 34 .
17.
Jafari A.A.
,
Mahmoudi H.
, and
Mirjalili B.F.
, J. Iran. Chem. Soc. , 2011 , 8 , 851 .
18.
Klapars A.
,
Antilla J.C.
,
Huang X.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2001 , 123 , 7727 .
19.
Yu C.-W.
,
Chen G.S.
,
Huang C.-W.
, and
Chern J.-W.
, Org. Lett. , 2012 , 14 , 3688 .
20.
Reddy V.P.
,
Kumar A.V.
, and
Rao K.R.
, Tetrahedron Lett. , 2011 , 52 , 777 .
21.
Boswell M.G.
,
Yeung F.G.
, and
Wolf C.
, Synlett , 2012 , 23 , 1240 .
