M. Xue et al.
[18] J. B. Baruah, K. Osakada, T. Yamamoto, J. Mol. Catal. A Chem. 1995,
101, 17.
one of the substrates,
silylation product was obtained (Table 3).
a high-selectivity dehydrogenative
[19] A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020.
[20] A. Ochida, M. Sawamura, Chem. Asian. J. 2007, 2, 609.
[21] C. Reyes, A. Prock, W. P. Giering, J. Organomet. Chem. 2003, 671, 13.
[22] J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 1945.
[23] A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176.
[24] N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002,
67, 5553.
In summary, a series of triarylphosphane (1a–11a) have been
synthesized. An X-ray crystal structure analysis of (2-bromo-
phenyl)diphenylphosphane 1a unambiguously confirmed the
constitution of the functionalized phosphane. Hydrosilylation
reactions of styrene with triethoxysilane catalyzed by RhCl3–
triarylphosphane were investigated. In comparison with all
catalysts, RhCl3–diphenyl(2-trimethylsilylphenyl)phosphane (8a)
exhibited higher activity as well as higher levels of β-adduct
selectivity. The results showed that substituents attached to
triarylphosphane ligands had a significant impact on the
rhodium-catalyzed hydrosilylation process. Further studies on
the structures of rhodium–triarylphosphane complexes and the
reaction mechanism are ongoing.
[25] S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem.
Int. Ed. 2004, 43, 1871.
[26] C. Baillie, J. L. Xiao, Tetrahedron 2004, 60, 4159.
[27] V. Leeuwen, W. N. M. Piet, J. Am. Chem. Soc. 2011, 133, 18562.
[28] I. Bonnaventure, A. B. Charette, J. Org. Chem. 2008, 73, 6330.
[29] F. S. Zhang, L. D. Wang, S. H. Chang, K. L. Huang, Dalton Trans. 2013,
42, 7111.
[30] G. J. Zhou, Q. Wang, X. Z. Wang, C. L. Ho, W. Y. Wong, D. G. Ma,
J. Mater. Chem. 2010, 20, 7472.
[31] J. Shin, J. Bertoia, K. R. Czerwinski, C. Bae, Green Chem. 2009, 11, 1576.
[32] V. Ravindar, H. Hemling, H. Schumann, J. Blum, Synth. Commun.
1992, 22, 841.
Acknowledgment
[33] G. Dmitri, J. Lei, B. Stephen, Org. Lett. 2003, 5, 2315.
[34] Y. H. Li, L. Q. Lu, S. Das, S. Pisiewicz, K. Junge, M. Beller, J. Am. Chem.
Soc. 2012, 134, 9727.
We are grateful to the Natural Science Foundation of China
(21203049) for financial support.
[35] R. Lindner, B. V. D. Bosch, M. Lutz, J. N. H. Reek, J. I. V. D. Vlugt,
Organometallics 2011, 30, 499.
[36] O. Herd, A. Hessler, M. Hingst, M. Tepper, O. Stelzer, J. Organomet.
Chem. 1996, 522, 69.
[37] S. Nobuaki, A. Tomoyuki, F. Tuyoshi, K. N. Hizuru, I. Toshihiko, Org.
Biomol. Chem. 2007, 5, 3762.
[38] S. S. Gunatilleke, A. M. Barrios, J. Inorg. Biochem. 2008, 102, 555.
[39] S. Tasan, O. Zava, B. Bertrand, C. Bernhard, C. Goze, M. Picquet,
Dalton Trans. 2013, 42, 6102.
References
[1] G. Wittig, U. Schollkopf, Chem. Ber. 1954, 87, 1318.
[2] M. Mikołajczyk, W. Perlikowska, J. Omelańczuk, H. J. Cristau,
A. Perraud-Darcy, J. Org. Chem. 1998, 63, 9716.
[3] R. Robiette, J. Richardson, V. K. Aggarwal, J. N. Harvey, J. Am. Chem.
Soc. 2006, 128, 2394.
[4] D. D. Díaz, S. S. Gupta, J. Kuzelka, M. Cymborowski, M. Sabat, M. G. Finn,
Eur. J. Inorg. Chem. 2006, 22, 4489.
[5] K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore,
J. Org. Chem. 1997, 62, 6726.
[40] J. Li, H. W. Fu, P. Hu, Z. L. Zhang, X. Li, Y. X. Cheng, Chem.-Eur. J. 2012,
18, 13941.
[41] V. Ravindar, H. Hemling, H. Schumann, J. Blum, Synth. Commun.
1992, 22, 841.
[6] T. Ruhland, S. D. Nielsen, P. Holm, C. H. Christensen, J. Comb. Chem.
2007, 9, 301.
[42] A. Kawachi, T. Yoshioka, Y. Yamamoto, Organometallics 2006, 25, 2390.
[43] Siemens, Stereochemical Workstation Operation manual, Release
3.4, Siemens Analytical X-ray Instruments, Madison, WI, 1989.
[44] G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112.
[45] W. Q. Wu, P. Qian, D. X. Dong, X. L. Hou, J. Am. Chem. Soc. 2008, 130,
9717.
[46] J. McNulty, K. Keskar, Eur. J. Org. Chem. 2012, 5462.
[47] Y. Bai, J. J. Peng, J. Y. Li, G. Q. Lai, Appl. Organomet. Chem. 2011,
25, 400.
[7] T. Y. S. But, P. H. Toy, Chem. Asian. J. 2007, 2, 1340.
[8] Y. H. Zhu, F. Yao, L. Lei, G. Q. Xiang, Chin. J. Org. Chem. 2007, 27, 545.
[9] P. Kočovský, A. V. Malkov, Chem. Eur. J. 2012, 18, 6873.
[10] O. Niyomura, T. Iwasawa, N. Sawada, M. Tokunaga, Y. Obora, Y. Tsuji,
Organometallics 2005, 24, 3468.
[11] A. Ochida, M. Sawamura, Chem. Asian. J. 2007, 2, 609.
[12] B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2001, 123, 12726.
[13] A. Onopchenko, E. T. Sabourin, J. Chem. Eng. Data 1988, 33, 64.
[14] J. B. Perales, D. L. Van Vranken, J. Org. Chem. 2001, 66, 7270.
[15] L. N. Lewis, K. G. Sy, G. L. Bryant, P. E. Donahue, Organometallics
1991, 10, 3750.
Supporting Information
[16] F. Alonso, R. Buitrago, Y. Moglie, A. Sepúlveda-Escribano, M. Yus,
Organometallics 2012, 31, 2336.
[17] C. Ma, J. Y. Li, J. J. Peng, Y. Bai, G. D. Zhang, W. J. Xiao, G. Q. Lai,
J. Organomet. Chem. 2013, 727, 28.
Additional supporting information may be found in the online
version of this article at the publisher’s web site.
wileyonlinelibrary.com/journal/aoc
Copyright © 2014 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2014, 28, 120–126