RSC Advances
Paper
without the use of any organic solvents. This material is highly 22 C. Kubis, M. Sawall, A. Block, K. Neymeyr, R. Ludwig,
robust, thermally stable and reusable for many consecutive A. Bçrner and D. Selent, Chem.–Eur. J., 2014, 20, 11921.
cycles without the addition of more precious metals. The reus- 23 I. Piras, R. Jennerjahn, R. Jackstell, A. Spannenberg,
ability may only be limited under high pressures (1000 psi or R. Franke and M. Beller, Angew. Chem., Int. Ed., 2011, 50, 280.
more) in the rhodium-catalyzed reaction. We believe that our 24 P. Wang, X. Liu, J. Yang, Y. Yang, L. Zhang, Q. Yang and C. Li,
simple synthetic strategy will open up a new area related to the J. Mater. Chem., 2009, 19, 8009.
attachment of functionalized ferrocene to metal oxide nano- 25 R. Abu-Reziq, H. Alper, D. Wang and M. L. Post, J. Am. Chem.
particle surfaces for various regio- and heterogeneous catalytic Soc., 2006, 128, 5279.
applications. The mechanism of action of the unusually high 26 (a) H. Zhang, Y. Zou, Y.-M. Wang, Y. Shen and X. Zheng,
selectivity and its asymmetric version (i.e., enantioselective
hydrogenation, allylic alkylation, Michael addition and cyclo-
propanation) are currently under process in our lab.
Chem.–Eur. J., 2014, 20, 7830; (b) Z.-M. Li, Y. Zhou,
D.-J. Tao, W. Huang, X.-S. Chen and Z. Yang, RSC Adv.,
2014, 4, 12160.
27 (a) H. Zhang, W. Yang and J. Deng, Polymer, 2015, 80, 115; (b)
L. Li, C. Zhou, H. Zhao and R. Wang, Nano Res., 2015, 83,
709.
Acknowledgements
MNS gratefully acknowledges the National Plan for Science, 28 (a) Y. Maegawa and S. Inagaki, Dalton Trans., 2015, 44,
Technology and Innovation (MAARIFAH)-King Abdulaziz City
for Science and Technology through the Science and Tech-
nology Unit at King Fahd University of Petroleum and Minerals
(KFUPM), the Kingdom of Saudi Arabia, award number 15-
NAN4650-04.
13007; (b) J. M. Bolivar, S. Schelch, T. Mayr and
B. Nidetzky, ACS Catal., 2015, 5, 5984; (c) M. Rimoldi,
D. Fodor, J. A. van Bokhoven and A. Mezzetti, Catal. Sci.
¨
Technol., 2015, 5, 4575; (d) A. R. McDonald, C. Muller,
D. Vogt, G. P. M. van Klink and G. van Koten, Green Chem.,
2008, 10, 424.
29 S. Zhou, M. Johnson and J. G. C. Veinot, Chem. Commun.,
2010, 46, 2411.
References
´
´
1 O. Baudoin, M. Cesario, D. Guenard and F. Gueritte, J. Org. 30 V. Polshettiwar, B. Baruwati and R. S. Varma, Chem.
Chem., 2002, 67, 1199.
Commun., 2009, 1837.
2 M. A. Gauthier and H.-A. Klok, Chem. Commun., 2008, 2591. 31 R. S. Varma, Pure Appl. Chem., 2013, 85, 1703.
3 D.-W. Ryu, D. N. Primer, J. C. Tellis and G. A. Molander, 32 S. Vellalath, I. Coric and B. List, Angew. Chem., Int. Ed., 2010,
Chem.–Eur. J., 2016, 22, 120.
49, 9749.
4 A. Brennfuhrer, H. Neumann and M. Beller, Angew. Chem., 33 M. Gemmeren, F. Lay and B. List, Aldrichimica Acta, 2014, 47,
Int. Ed., 2009, 48, 4114.
3.
5 T. Rybak and D. G. Hall, Org. Lett., 2015, 17, 4156.
34 V. Polshettiwar and R. S. Varma, Green Chem., 2010, 12, 743.
6 R. Liu, M. Zhang, T. P. Wyche, G. N. Winston-McPherson, 35 C. O. Dalaigh, S. A. Corr, Y. Gunko and S. J. Connon, Angew.
T. S. Bugni and W. Tang, Angew. Chem., Int. Ed., 2012, 51,
7503.
7 J. K. Stille, Angew. Chem., Int. Ed., 1986, 25, 508–524.
8 R. F. Heck, Acc. Chem. Res., 1979, 12, 146.
9 N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.
10 A. Suzuki, Chem. Commun., 2005, 4759.
Chem., Int. Ed., 2007, 46, 4329.
36 Z. Wang, Y. Yu, Y. X. Zhang, S. Z. Li, H. Qian and Z. Y. Lin,
Green Chem., 2015, 17, 413.
37 F. Zhang, J. Jin, X. Zhong, S. Li, J. Niu, R. Li and J. Ma, Green
Chem., 2011, 13, 1238.
38 A. J. Amali and R. K. Rana, Green Chem., 2009, 11, 1781.
11 K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 39 B. Baruwati, D. Guin and S. V. Manorama, Org. Lett., 2007, 9,
1972, 94, 4374. 5377.
12 T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110, 1147. 40 V. Polshettiwar and R. S. Varma, Org. Biomol. Chem., 2009, 7,
13 N. T. S. Phan, M. V. D. Sluys and C. W. Jones, Adv. Synth.
Catal., 2006, 348, 609.
37.
41 C. Duanmu, L. Wu, J. Gu, X. Xu, L. Feng and X. Gu, Catal.
Commun., 2014, 48, 45.
14 F. Ungvary, Coord. Chem. Rev., 2007, 251, 2087.
15 H. A. Dieck and R. F. Heck, J. Am. Chem. Soc., 1974, 96, 1133. 42 M. N. Shaikh, M. Bououdina, A. A. Jimoh, M. A. Aziz,
16 R. F. Heck, Pure Appl. Chem., 1978, 50, 691.
17 W. A. Herrmann, C. Brobmer, K. Ofele, M. Beller and
H. Fischer, J. Mol. Catal. A: Chem., 1995, 103, 133.
18 Y. Bendavid, M. Portnoy, M. Gozin and D. Milstein,
Organometallics, 1992, 11, 1995.
A. Helal, A. S. Hakeem, Z. H. Yamani and T.-J. Kim, New J.
Chem., 2015, 39, 7293.
43 M. N. Shaikh, V. D. M. Hoang and T.-J. Kim, Bull. Korean
Chem. Soc., 2009, 30, 3075.
44 H.-K. Kim, J.-A. Park, K. M. Kim, M. N. Shaikh, D.-S. Kang,
J. Lee, Y. Chang and T.-J. Kim, Chem. Commun., 2010, 46,
8442.
19 M. Portnoy, Y. Bendavid and D. Milstein, Organometallics,
1993, 12, 4734.
20 T. Jia, P. Cao, B. Wang, Y. Lou, X. Yin, M. Wang and J. Liao, J. 45 G.-H. Hwang, E.-S. Ryu, D.-K. Park, S. C. Shim, C. S. Cho,
Am. Chem. Soc., 2015, 137, 13760.
21 C. Godard, S. B. Duckett, S. Polas, R. Tooze and
A. C. Whitwood, Dalton Trans., 2009, 14, 2496.
T.-J. Kim, J. H. Jeong and M. Cheong, Organometallics,
2001, 20, 5784.
41694 | RSC Adv., 2016, 6, 41687–41695
This journal is © The Royal Society of Chemistry 2016