5430
M. U. Raja et al. / Tetrahedron Letters 52 (2011) 5427–5430
Chapter 37; (d) Tietze, L. F.; Kettschau, G.; Heuschert, U.; Nordmann, G. Chem.
Eur. J. 2001, 7, 368–373.
10. Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361–1362.
11. Herrmann, W. A.; Boehm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999,
576, 23–41.
search Fellowship (SRF). We thank DST-India (FIST programme) for
the use of Bruker Smart APEX II diffractometer at the School of
Chemistry, Bharathidasan University.
12. Beletskaya, I. P.; Chuchuryukin, A. V.; van Koten, G.; Dijkstra, H. P.; van Klink, G.
P. M.; Kashin, A. N.; Nefedov, S. E.; Eremenko, I. L. Russ. J. Org. Chem. 2003, 39,
1268–1281.
Supplementary data
13. Bader, R. R.; Baumeister, P.; Blaser, H. U. Chimia 1996, 50, 99–105.
14. Zapf, A.; Beller, M. Top. Catal. 2002, 19, 101–109.
15. Tucker, C. E.; de Vries, J. G. Top. Catal. 2002, 19, 111–118.
16. Srinivas, P.; Srinivas, K.; Likhar, P. R.; Sridharb, B.; Mohan, K. V.; Bhargava, S.;
Kantam, M. L. J. Org. Chem. 2011, 696, 795–801.
17. (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2002, 43, 4955–4957; (b) Gossage, P.
A.; Jenkins, A.; Yadav, P. N. Tetrahedron Lett. 2004, 45, 7689–7691; (c) Lee, S. J.
Organomet. Chem. 2006, 691, 1347–1355.
18. (a) Demertzi, D. M.; Yadav, P. N.; Demertzis, M. A.; Jasiski, J. P.; Andreadakic, F.
J.; Kostas, I. D. Tetrahedron Lett. 2005, 45, 2923–2926; (b) Demertzi, D. M.;
Kourkoumelis, N.; Derlat, K.; Michalak, J.; Andreadaki, F. J.; Kostac, I. D. Inorg.
Chim. Acta 2008, 361, 1562–1565; (c) Paul, P.; Datta, S.; Halder; Acharyya, R.;
Basuli, F.; Butcher, R. J.; Peng, S. M.; Lee, G. H.; Castineiras, A.; Drew, M. G. B.;
Bhattacharya, S. J. Mol. Catal. A: Chem 2011, 344, 62–73.
19. Saito, S.; Saika, M.; Yamasaki, R.; Azumaya, I.; Masu, H. Organometallics 2011,
30, 1366–1373.
20. Dıez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics
2003, 22, 4610–4612.
21. Srinivas, P.; Likhar, P. R.; Maheswaran, H.; Sridhar, B.; Ravikumar, K.; Kantam,
M. L. Chem. Eur. J. 2009, 15, 1578–1581.
22. Yoon, M. S.; Ryu, D.; Kim, J.; Ahn, K. H. Organometallics 2006, 25, 2409–2411.
23. Mino, T.; Shirae, Y.; Sasai, Y.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2006, 71,
6834–6839.
24. Wang, H.; Liu, J.; Deng, Y.; Min, T.; Yu, G.; Wu, X.; Yang, Z.; Lei, A. Chem. Eur. J.
2009, 15, 1499–1507.
25. (a) Venkatachalam, G.; Ramesh, R. Tetrahedron Lett. 2005, 46, 5215–5218; (b)
Ulaganatha Raja, M.; Ramesh, R.; Ahn, K. H. Tetrahedron Lett. 2009, 50, 7014–
7017.
26. Typical Procedure for the Heck Reaction: The reaction vessel was charged with
bromobenzene (1 mmol), alkene (2 mmol), K2CO3 (1.2 mmol), and the catalyst
(1 mol %) in N,N-dimethylformamide (2 ml). The reaction mixture was heated
to 150 °C, and the progress of reaction was monitored by TLC. At the end of the
reaction, the reaction mixture was cooled to room temperature, diluted with
EtOAc, and washed with 1 N aq HCl and water. The combined organic phase
was dried over anhydrous Na2SO4. After removal of the solvent, the residue
was subjected to column chromatography on silica gel using ethyl acetate and
hexane mixtures to afford the coupled product in high purity.
Crystallographic data for the structural analysis have been
deposited with Cambridge crystallographic center, CCDC No.
814963. Copies of this information may be obtained free of charge
from The Director, CCDC, 12 Union roads, Cambridge CB2 1EZ, UK
(email: deposit@ccdc.cam.ac.uk). Complete sets of refined posi-
tional coordinates as well as anisotropic thermal parameters and
complete tabulations of bond lengths and bond angles). Supple-
mentary data associated with this article can be found, in the on-
References and notes
1. Heck, R. F. Acc. Chem. Res. 1979, 12, 146–152.
2. (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London,
UK, 1985; (b) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.,
Flemming, I., Eds.; Pergamon: New York, 1991; vol. 4,. Chapter 4.3 (c) Tsuji, J.
Palladium Reagents and Catalysts; John Wiley: Chichester, UK, 1995; (d) Brase,
S.; de Meijere, A. In Metal Catalyzed Cross Coupling Reactions; Diederich, F.,
Stang, P. J., Eds.; Wiley: New York, 1998. Chapter 3; (e) de Meijere, A.; Meyer, F.
E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379–2411; (f) Crisp, G. T. Chem. Soc.
Rev. 1998, 27, 427–436; (g) Casey, M.; Lawless, J.; Shirran, C. Polyhedron 2000,
19, 517–520.
3. (a) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2–7; (b) Beletskaya, I. P.;
Cheprakov, A. V. Chem. Rev. 2000, 100, 3009–3066.
4. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771–11835.
5. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651–2710.
6. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
7. Srinivas, P.; Srinivas, K.; Likhar, P. R.; Sridhar, B.; Mohan, K. V.; Bhargava, S.;
Kantam, M. L. J. Organomet. Chem. 2011, 696, 795–801.
8. (a) Heck, R. F. Org. React. 1982, 27, 345–390; (b) Spencer, A. J. Organomet. Chem.
1983, 258, 101–108.
9. (a) Overman, L. F.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042–
2044; (b) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: New
York, 1996. Chapter 31; (c)Catalysis of Organic Reactions; de Vries, R. A.,
Vosejpka, P. C., Ash, M. L., Herkes, F. E., Eds.; Marcel Dekker: New York, 1998.