N. Iranpoor et al.
[
9] B. Sreedhar, R. Arundhathi, M. Amarnath, G. Parthasarathy, Appl. Clay
Sci. 2009, 43, 425.
4
5% conversion. The reaction mixture was filtered off to remove the
catalyst and the filtrate was left to react further. ICP analysis of the fil-
trate showed 2.5% of Pd leaching. GC analysis showed that after 1.5 h
only 55% conversion had occurred. This observation demonstrates
that the solid catalyst had the main function as a heterogeneous cat-
alyst in this catalytic system.
A mechanistic pathway was proposed (Fig. 2). Pd(II) was reduced
by SDPP to the nanoparticles of Pd(0), followed by the oxidative
addition of aryl halide to give the aryl palladium species (1a). This
species could then react with species 2a to produce 3a, which
underwent reductive elimination to give the product together with
the regenerated Pd(0) catalyst (Fig. 2).
[
[
10] Y. Luo, J. Wu, Tetrahedron Lett. 2009, 50, 2103.
11] a) M. Kim, J. Lee, H. Y. Lee, S. Chang, Adv. Synth. Catal. 2009, 351, 1807;
b) M. Kim, J. Kwak, S. Chang, Angew. Chem. Int. Ed. 2009, 48, 8935;
c) M. Kim, S. Chang, Org. Lett. 2010, 12, 1640; d) J. Kwak, M. Kim,
S. Chang, J. Am. Chem. Soc. 2011, 133, 3780.
12] H. J. Kim, M. Kim, S. Chang, Org. Lett. 2011, 13, 2368.
13] a) G. Liu, J. R. Huth, E. T. Olejniczak, R. Mendoza, P. Devries, S. Leitza,
E. B. Reilly, G. F. Okasinski, S. W. Fesik, T. W. Geldern, J. Med. Chem.
[
[
2
001.44, 1202; b) S. F. Nielsen, E. O. Nielsen, G. M. Olsen, T. Liljefors,
D. Peters, J. Med. Chem. 2000, 43, 2217; c) P. S. Luo, M. Yu, R. Y. Tang,
P. Zhang, J. H. Hi, Tetrahedron Lett. 2009, 50, 1065; d) S. I. Murahashi,
M. Yamamura, K. I. Yanagisawa, N. Mita, K. Kondo, J. Org. Chem.
1
979, 44, 2408; e) D. J. C. Prasad, G. Sekar, Org. Lett. 2011, 13, 1008.
[
14] T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205.
Conclusion
[15] J. Lindley, Tetrahedron 1984, 40, 1433.
[
[
[
16] T. Migita, T. Shimizu, Y. Asami, J. Shiobara, Y. Kato, M. Kosugi, Bull.
We have developed a useful and efficient procedure for preparation
of aryl ethers and aryl thioethers in good to excellent yields by a
catalytic coupling reaction between phenols or thiophenols and aryl
halides using nanoparticles of Pd(0)/SDPP as catalyst. The method is
applicable to aryl iodides, bromides as well as chlorides and was also
found to be useful for coupling of benzyl thiol. The ease of synthesis
and recyclability of the catalyst together with the mild reaction
conditions make this method very useful for this transformation.
Chem. Soc. Jpn. 1980, 53, 1385.
17] a) V. Percec, J. Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 6895; b)
Y. G. Zhang, K. C. Ngeow, J. Y. Ying, Org. Lett. 2007, 9, 3495.
18] a) C. Mispelaere-Canivet, J. F. Spindler, S. Perrio, P. Beslin,
Tetrahedron 2005, 61, 5253;
b) T. Itoh, T. Mase, Org. Lett. 2004, 6, 4587; c) M. A. Fernandez-
Rodriguez, Q. L. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006,
128, 2180; d) M. Murata, S. L. Buchwald, Tetrahedron 2004, 60,
7397; e) U. Schopfer, A. Schlapbach, Tetrahedron 2001, 57,
3069; g) N. Zheng, J. C. Williams, F. J. Fleitz, J. D. Armstrong, R.
P. Volante, J. Org. Chem. 1998, 63, 9606; h) G. Mann, D.
Baranano, J. F. Hartwig, A. L. Rheingold, I. A. Guzei, J. Am. Chem.
Soc. 1998, 120, 9205; i) C. C. Eichman, J. P. Stambuli, J. Org.
Chem. 2009, 74, 4005; j) Z. Jiang, J. She, X. F. Lin, Adv. Synth.
Catal. 2009, 351, 2558.
Acknowledgments
We are grateful to Shiraz University Research Council for
partial support of this work and to Dr Motevalli for her kind
technical assistance.
[
[
19] A. Correa, M. Carril, C. Bolm, Angew. Chem. Int. Ed. 2008, 47, 2880.
20] a) Y. C. Wong, T. T. Jayanth, C. H. Cheng, Org. Lett. 2006, 8, 5613; b)
M. Kidwai, N. K. Mishra, V. Bansal, A. Kumar, S. Mozumdar, Tetrahe-
dron Lett. 2007, 48, 8883; c) B. A. Wang, R. S. Zeng, H. Q. Wei, A. Q.
Jia, J. P. Zou, Chinese J. Chem. 2006, 24, 1062.
References
[
[
[
1] a) K. C. Nicolaou, S. Natarajan, H. Li, N. F. Jain, R. Hughes, M. E.
Solomon, J. M. Ramanjulu, C. N. C. Boddy, M. Takayanagi, Angew.
Chem. Int. Ed. 1998, 37, 2708; b) D. A. Evans, J. L. Katz, T. R. West,
Tetrahedron Lett. 1998, 39, 2937.
2] a) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson,
B. W. Trotter, J. L. Katz, Angew. Chem. Int. Ed. 1998, 37, 2704;
b) K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem.
Int. Ed. 1999, 38, 2096.
3] a) H. Deng, J. K. Jung,T. Liu, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda,
J. Am. Chem. Soc. 2003, 125, 9032; b) D. S. Surry, S. L. Buchwald, Chem.
Sci. 2011, 2, 27; c) D. S. Surry, S. L. Buchwald, Chem. Sci. 2010, 1, 13; d)
F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2009, 48, 6954; e) D. Ma,
Q. Cai, Acc. Chem. Res. 2008, 41, 1450; f) F. Monnier, M. Taillefer,
Angew. Chem. Int. Ed. 2008, 47, 3096; g) I. P. Beletskaya, A. V.
Cheprakov, Chem. Rev. 2004, 248, 2337; h) S. V. Ley, A. W. Thomas,
Angew. Chem. Int. Ed. 2003, 42, 5400; i) K. Kunz, U. Scholz, D.
Ganzer, Synlett 2003, 24, 28; j) A. R. Muci, S. L. Buchwald, Top. Curr.
Chem. 2002, 219, 131; k) J. F. Hartwig, Angew. Chem. Int. Ed. 1998,
[21] a) F. Y. Kwong, S. L. Buchwald, Org. Lett. 2002, 4, 3517; b) N. Taniguchi,
Synlett 2006, 1351; c) Y. J. Chen, H. H. Chen, Org. Lett. 2006, 8, 5609; d)
L. Rout, T. K. Sen, T. Punniyamurthy, Angew. Chem. Int. Ed. 2007, 46,
5583; e) L. Cai, J. Cuevas, Y. Y. Peng, V. W. Pike, Tetrahedron Lett.
2006, 47, 4449; f) S. Bhadra, B. Sreedhar, B. C. Ranu, Adv. Synth. Catal.
2009, 351, 2369.
[
22] a) D. Zhu, L. Xu, F. Wu, B. S. Wan, Tetrahedron Lett. 2006, 47, 5781;
b) S. Jammi, P. Barua, L. Rout, P. Saha, T. Punnlyamurthy, Tetrahe-
dron Lett. 2008, 49, 1484; c) C. G. Bates, P. Saejueng, M. Q. Doherty,
D. Venkataraman, Org. Lett. 2004, 6, 5005; d) D. W. Ma, S. W. Xie,
P. Xue, X. J. Zhang, J. H. Dong, Y. W. Jiang, Angew. Chem. Int. Ed.
2
009, 48, 4222; e) Z. Y. Duan, S. Ranjit, P. F. Zhang, X. G. Liu,
Chem. Eur. J. 2009, 15, 3666; f) S. Kumar, L. Engman, J. Org. Chem.
006, 71, 5400; g) N. Taniguchi, J. Org. Chem. 2007, 72, 1241; h)
2
O. Baldovino-Pantaleon, S. Hernandez-Ortega, D. Morales-
Morales, Adv. Synth. Catal. 2006, 348, 236.
[23] I. W. J. Still, F. D. Toste, J. Org. Chem. 1996, 61, 7677.
[24] M. Kuhn, F. C. Falk, J. Paradies. Org. Lett. 2011, 13, 4100.
[25] H. Firouzabadi, N. Iranpoor, M. Gholinejad, Adv. Synth. Catal. 2010,
3
7, 2047.
[
4] a) R. Frlan, D. Kikelj, Synthesis 2006, 14, 2271; b) J. S. Sawyer,
3
52, 119.
Tetrahedron 2000, 56, 5045.
[
26] a) N`. Iranpoor, H. Firouzabadi, R. Azadi, Eur. J. Org. Chem. 2007, 13, 2197;
b) N. Iranpoor, H. Firouzabadi, R. Azadi, J. Organomet. Chem. 2008, 693,
2469; c) N. Iranpoor, H. Firouzabadi, R. Azadi, J. Organomet. Chem.
2010, 695, 887.
[
[
5] G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
6] a) A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. Int. Ed. 1995,
34, 1348; b) J. Louie, J. F. Hartwig, Tetrahedron Lett. 1995, 36, 3609.
[
7] a) D. M. T. Chan, K. L. Monaco, R. P. Wang, M. P. Winters,
Tetrahedron Lett. 1998, 39, 2933; b) D. A. Evans, J. L. Katz, T. R.
West, Tetrahedron Lett. 1998, 39, 2937; c) P. Y. S. Lam, C. G. Clark,
S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs,
Tetrahedron Lett. 1998, 39, 2941.
[27] N. Iranpoor, H. Firouzabadi, A. Tarassoli, M. Fereidoonnezhad,
Tetrahedron 2010, 66, 2415.
[28] H. Firouzabadi, N. Iranpoor, M. Gholinejad, J. Mol. Catal. A: Chem.
2010, 321, 110.
[29] N. Iranpoor, H. Firouzabadi, S. Motevalli, M. Talebi, J. Organomet. Chem.
2012, 708–709, 118.
[
8] R. Arundhathi, B. Sreedhar, G. Parthasarathy, Appl. Clay Sci. 2011,
5
1, 131.
[30] N. Iranpoor, H. Firouzabadi, A. Jamalian, F. Kazemi, Tetrahedron 2005, 61, 5699.
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