Abstract
Palladium substituted in cerium dioxide in the form of a solid solution, Ce0·98 Pd0·02 O1·98 is a new heterogeneous catalyst which exhibits high activity and 100% trans-selectivity for the Heck reactions of aryl bromides including heteroaryls with olefins. The catalytic reactions work without any ligand. Nano-crystalline Ce0·98 Pd0·02 O1·98 is prepared by solution combustion method and Pd is in +2 state. The catalyst can be separated, recovered and reused without significant loss in activity.
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References
de Meijere A and Meyer F E 1994 Angew. Chem. Int. Ed. 33 2379
Beletskaya A P and Cheprakov V 2000 Chem. Rev. 100 3009; Whitcombe N J and Hii K K M, Gibson S E 2001 Tetrahedron 57 7449
Crisp GT 1998 Chem. Soc. Rev. 27 427; Dieck H A and Heck R F 1974 J. Am. Chem. Soc. 96 1133
de Vries Johannes G 2001 Can. J. Chem. 79 1086
Burke T R, Liu D G and Gao Y J 2000 J. Org. Chem. 65 6288; Haberli A and Leumann C J 2001 Org. Lett. 3 489; de Meijere A and Meyer F E 1994 Angew. Chem. 106 2473
Biffis A, Zecca M, Basato M 2001 J. Mol. Catal. A 173 249
Hillier A C, Grasa G A, Viciu M S, Lee H M, Yang C and Nolan S P 2002 J. Organomet. Chem. 653 69; Selvakumar K, Zapf A and Beller M 2002 Org. Lett. 4 3031; Yao C, Li H, Wu H, Liu Y and Wu P 2009 Catal. Commun. 10 1099
Hallberg A and Westfelt L 1984 J. Chem. Soc. Perkin Trans. 1 933
Wan Y, Wang H, Zhao Q, Klingstedt M, Terasaki O and Zhao D 2009 J. Am. Chem. Soc. 131 4541.
Kaneda K, Higuchi M and Imanaka T 1990 J. Mol. Catal. 63 L33
Wali A, Pillai S M, Kaushik V K and Satish S 1996 Appl. Catal. A 135 83
Mehnert C P, Weaver D W and Ying J Y 1998 J. Am. Chem. Soc. 120 12289
Ding J H and Gin D L 2000 Chem. Mater. 12 22
Djakovitch L and Koehler K 2001 J. Am. Chem. Soc. 123 5990
Dams M, Drijkoningen L, Pauwels B, van Tendeloo G, de Vos D E and Jacobs P A 2002 J. Catal. 209 225; Basu B, Das S, Das P, Mandal B, Banerjee D and Almqvist F 2009 Synthesis 7 1137
Choudary B M, Madhi S, Chowdari N S, Kantam M L and Sreedhar B 2002 J. Am. Chem. Soc. 124 14127
Corma A, Garcia H, Leyva A and Primo A 2003 Appl. Catal. A 247 41
Ranting T, Shiding M, Zhimin L, Yun X, Buxing H, Guimin A and Kunlun D 2009 Green Chem. 11 96
Cwik A, Hell Z and Figureas F 2006 Adv. Synth. Catal. 348 523
Kantam M L, Shiva Kumar K B, Srinivas P and Sreedhar B 2007 Adv. Synth. Catal. 349 1141
Hegde M S, Madras G and Patil K C 2009 Acc. Chem. Res. 42 704 and references therein
Bera P, Patil K C, Jayaram V, Subbanna G N and Hegde M S 2000 J. Catal. 196 293
Priolkar K R, Bera P, Sarode P R, Hegde M S, Emura S, Kumashiro R and Lalla N P 2002 Chem. Mater. 14 2120
Mori K, Yamaguchi K, Hara T, Muzugaki T, Ebitani K and Kaneda K 2002 J. Am. Chem. Soc. 124 11572; Molnar A, Papp A, Miklos K and Forgo P 2003 Chem. Commun. 20 2626; Daku K M L, Newton R F, Pearce S P, Vile J and Williams J M J 2003 Tet. Let. 44 5095; Phan N T S, Brown D H, Adams H, Spey S E and Styring P 2004 Dalton Trans. 9 1348
Hagiwara H, Sugawara Y, Isobe K, Hoshi T and Suzuki T 2004 Org. Lett. 6 2325; Hagiwara H, Sugawara Y, Hoshi T and Suzuki T 2005 Chem. Commun. 2942
Link JT and Overman L E 1998 Metal-catalyzed cross-coupling reactions, (eds.: F. Diederich, P. J. Stang) Weinheim; Wiley-VCHVerlag p. 231
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This work was supported by the Department of Science and Technology (DST) and Council of Scientific and Industrial Research (CSIR), New Delhi. The authors also thank the NMR Research Centre (NRC), Indian Institute of Science, for providing NMR spectra.
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NMR data of line products are given in the supporting information (see www.ias.ac.in/chemsci).
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SANJAYKUMAR, S.R., MUKRI, B.D., PATIL, S. et al. Ce0·98Pd0·02O2-δ: Recyclable, ligand free palladium(II) catalyst for Heck reaction. J Chem Sci 123, 47–54 (2011). https://doi.org/10.1007/s12039-011-0103-6
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DOI: https://doi.org/10.1007/s12039-011-0103-6