Abstract
Nanosized perovskite-type SmFeO3 powder, prepared through the thermal decomposition of Sm[Fe(CN)6].4H2O with an average particle diameter of 28 nm and a specific surface area of 42 m2 g−1, was used as a recyclable heterogeneous catalyst for the efficient and selective reduction of aromatic nitro compounds into the corresponding amines by using propan-2-ol as a hydrogen donor (reducing agent) and KOH as a promoter under microwave irradiation. This highly regio- and chemoselective catalytic method is fast, clean, inexpensive, high yielding and also compatible with the substrates containing easily reducible functional groups. In addition, the nanosized SmFeO3 catalyst can be reused without loss of activity.
References
1.
Larock R.C.
, Comprehensive organic transformations: a guide to functional group preparation , 2nd edn, Wiley-VCH : Weinheim , 1999 , pp. 821 –828 .
2.
Hudlicky M.
, Reductions in organic chemistry , 2nd edn, ACS Monograph , 1996 .
3.
Schilling S.L.
, Kirk-Othmer encyclopaedia of chemical technology , 4th edn, John Wiley & Sons , 1991 , Vol. 2 , pp. 482 –503 .
4.
Marlic C.A.
,
Motamed S.
, and
Quinn B.
, J. Org. Chem. , 1995 , 60 , 3365 .
5.
Liu Y.
,
Lu Y.
,
Prashad M.
,
Repic O.
, and
Blacklock T.J.
, Adv. Synth. Catal. , 2005 , 347 , 217 .
6.
Pitts M.R.
,
Harrison J.R
, and
Moody C.
, J. Chem. Soc. Perkin Trans. 1 , 2001 , 955 .
7.
Nagaraja D.
, and
Pasha M.A.
, Tetrahedron Lett. , 1999 , 40 , 7855 .
8.
Lee H.Y.
, and
An M.
, Bull. Korean Chem. Soc. , 2004 , 25 , 1717 .
9.
Iyer S.
, and
Kulkarni G.M.
, Synth. Commun. , 2004 , 34 , 721 .
10.
De P.
, Synlett , 2004 , 1835 .
11.
Vass A.
,
Dudar J.
, and
Varma R.S.
, Tetrahedron Lett. , 2001 , 42 , 5347 .
12.
Gowda S.
, and
Gowda D.C.
, Ind. J. Chem. , 2003 , 42B , 180 .
13.
Meshram H.M.
,
Ganesh Y.S.S.
,
Sekhar K.C.
, and
Yadav J.S.
, Synlett , 2000 , 993 .
14.
Bae J.W.
,
Cho Y.J.
,
Lee S.H.
, and
Yoon C.M.
, Tetrahedron Lett , 2000 , 41 , 175 .
15.
Sadavarte V.S.
,
Swami S.S.
, and
Desai D.G.
, Synth. Commun. , 1998 , 28 , 1139 .
16.
Srinivasa G.R.
,
Abiraj K.
, and
Gowda D.C.
, Ind. J. Chem. , 2003 , 42B , 2882 .
17.
Gowda S.
,
Gowda B.K.K.
, and
Gowda D.C.
, Synth. Commun. , 2003 , 33 , 281 .
18.
Hirao T.
,
Shiori J.
, and
Okahata N.
, Bull. Chem. Soc. Jpn. , 2004 , 77 , 1763 .
19.
Gowda D.C.
,
Gowda A.S.P.
, and
Baba A.R.
, Synth. Commun. , 2000 , 30 , 2889 .
20.
Iyer S.
, and
Sattar A.K.
, Synth. Commun. , 1998 , 28 , 1721 .
21.
Kumbhar P.S.
,
Valnte J.S.
, and
Figueras F.
, Tetrahedron Lett. , 1998 , 39 , 2573 .
22.
Yadav G.D.
, and
Lande S.V.
, Adv. Synth. Catal. , 2005 , 347 , 1235 .
23.
Basu M.K.
,
Becker F.F.
, and
Banik B.K.
, Tetrahedron Lett. , 2000 , 41 , 5603 .
24.
Gowda S.
, and
Gowda D.C.
, Tetrahedron Lett. , 2002 , 58 , 2211 .
25.
Kumar J.S.D.
,
Ho M.M.
, and
Toyokuni T.
, Tetrahedron Lett. , 2001 , 42 , 5601 .
26.
McLaughlin M.A.
, and
Barnes D.M.
, Tetrahedron Lett. , 2001 , 41 , 5347 .
27.
Pogorelic
,
Filipan-Litvic M.
,
Merkas S.
,
Ljubic G.
,
Cepanec L.
, and
Litvic M.
, J. Mol. Catal. A: Chem. , 2007 , 274 , 202 .
28.
Pehlivan L.
,
Metay E.
,
Laval S.
,
Dayoub W.
,
Demonchaux P.
,
Mignani G.
,
Lemaire M.
, Tetrahedron Lett. , 2010 , 51 , 1939 .
29.
Rylander P.
, Catalytic hydrogenation in organic synthesis , Academic Press , New York , 1979 , pp. 114 –134 .
30.
Dale D.J.
,
Dunn P.J.
,
Golightly C.
,
Hughes M.L.
,
Levett P.C.
,
Pearce A.K.
,
Searle P.M.
,
Ward G.W.
, and
Wood A.S.
, Org. Process Res. Dev. , 2000 , 4 , 17 .
31.
Hoogenraad M.
,
van der Linden J.B.
,
Smith A.A.
,
Hughes B.
,
Derrick A.M.
,
Harris L.J.
,
Higginson P.D.
,
Pettman A.J.
, Org. Process Res. Dev. , 2004 , 8 , 469 .
32.
Johnstone R.A.W.
,
Wilby A.H.
, and
Entwistle I.D.
, Chem. Rev. , 1985 , 85 , 129 .
33.
Gowda D.C.
, and
Mahesha B.
Synth. Commun. , 2000 , 30 , 3639 .
34.
Sonavane
, and
Jayaram R.V.
, Synlett , 2004 , 146 .
35.
Selvam P.
,
Sonavane S.U.
,
Mohopatra S.K.
, and
Jayaram R.V.
, Adv. Synth. Catal. , 2004 , 346 , 542 .
36.
Wen H.
,
Yao K.
,
Zhang Y.
,
Zhou Z.
,
Kirschning A.
, Catal. Commun. , 2009 , 10 , 1207 .
37.
Chen Y.
,
Qiu J.
,
Wan X.
, and
Xiu J.
, J. Catal. , 2006 , 242 , 227 .
38.
Russo N.
,
Fino D.
,
Saracco G.
, and
Specchia V.
, J. Catal. , 2005 , 229 , 459 .
39.
De Bruijn F.
, Green Chem. , 2005 , 7 , 132 .
40.
Zhou B.
,
Han S.
,
Raja R.
, and
Somorjai G.A.
, Nanotechnology in catalysis , Springer , New York , 2007 .
41.
Caddick S.
, and
Fitzmaurice R.
, Tetrahedron , 2009 , 65 , 3325 .
42.
Farhadi S.
, and
Zaidi M.
, J. Mol. Catal. A: Chem. , 2009 , 299 , 18 .
43.
Farhadi S.
, and
Panahandehjoo S.
, Appl. Catal. A: Gen. , 2010 , 382 , 293 .
44.
Farhadi S.
,
Momeni M.
, and
Taherimehr M.
, J. Alloys Compd. , 2009 , 471 , L5 .
45.
Quignard F.
,
Graziani O.
, and
Choplin A.
, Appl. Catal. A: Gen. , 1999 , 182 , 29 .
46.
Buckingham J.
(ed.) Dictionary of organic compounds , 6th edn, Chapman-Hall , London , 1996 .