Catalysis Science & Technology
Paper
G. L. Zhang, Green Chem., 2011, 13, 2939; ( f ) P. Dutta and A. Sarkar,
Adv. Synth. Catal., 2011, 353, 2814; (g) H. Gruber-Woelfler,
P. F. Radaschitz, P. W. Feenstra, W. Haas and J. G. Khinast,
J. Catal., 2012, 286, 30; (h) N. Iranpoor, H. Firouzabadi, S. Motevalli
and M. Talebi, J. Organomet. Chem., 2012, 708–709, 118; (i) S. Farsadpour,
The excellent catalytic performance and easy separation make
this catalyst a promising alternative to other supported Pd
catalysts.
¨
L. T. Ghoochany, S. Shylesh, G. Dorr, A. Seifert, S. Ernst and W. R. Thiel,
ChemCatChem, 2012, 4, 401.
Acknowledgements
¨
¨
9 (a) S. S. Soomro, R. Rohlich and K. Kohler, Adv. Synth. Catal., 2011,
353, 767; (b) X. Li, X. Y. Yan, H. H. Chang, L. C. Wang, Y. Zhang,
W. W. Chen, Y. W. Li and W. L. Wei, Org. Biomol. Chem., 2012,
10, 495; (c) Y. Y. Ma, X. B. Ma, Q. Wang and J. Q. Zhou, Catal. Sci.
Technol., 2012, 2, 1879.
We are grateful for the financial support from the Natural Science
Foundation of Jiangsu Province of China (No. BK2010485), and the
Science and Technology Development Fund of Nanjing University
of Science and Technology (No. XKF09066).
10 (a) C. Venkatesan and A. P. Singh, J. Catal., 2004, 227, 148;
(b) M. J. Jin, A. Taher, H. J. Kang, M. Choi and R. Ryoo, Green
Chem., 2009, 11, 309.
References
11 (a) J. S. Chen, A. N. Vasiliev, A. P. Panarello and J. G. Khinast, Appl.
Catal., A, 2007, 325, 76; (b) P. Y. Wang, Z. Y. Wang, J. G. Li and
Y. X. Bai, Microporous Mesoporous Mater., 2008, 116, 400; (c) M. Choi,
D. H. Lee, K. Na, B. W. Yu and R. Ryoo, Angew. Chem., Int. Ed., 2009,
48, 3673; (d) G. Z. Fan, B. Zou, S. Q. Cheng and L. H. Zheng, Ind. Eng.
Chem. Res., 2010, 16, 220; (e) L. Huang, T. P. Ang, Z. Wang, J. Tan,
J. H. Chen and P. K. Wong, Inorg. Chem., 2011, 50, 2094.
12 (a) K. Marubayashi, S. Takizawa, T. Kawakusu, T. Arai and H. Sasai,
Org. Lett., 2003, 5, 4409; (b) S. U. Son, I. K. Park, J. Park and
T. Hyeon, Chem. Commun., 2004, 778; (c) M. K. Schroter,
L. Khodeir, M. W. E. van den Berg, T. Hikov, M. Cokoja, S. Miao,
W. Grunet, M. Muhler and R. A. Fischer, Chem. Commun., 2006,
2498; (d) P. P. Fang, A. Jutand, Z. Q. Tian and C. Amatore, Angew.
Chem., Int. Ed., 2011, 50, 12184; (e) S. Moussa, A. R. Siamaki,
B. F. Gupton and M. S. El-Shall, ACS Catal., 2012, 2, 145;
( f ) A. Fihri, D. Cha, M. Bouhrara, N. Almana and V. Polshettiwar,
ChemSusChem, 2012, 5, 85.
13 (a) A. Saha, J. Leazer and R. S. Varma, Green Chem., 2012, 14, 67;
(b) B. Baruwati, D. Guin and S. V. Manorama, Org. Lett., 2007,
9, 5377; (c) D. Guin, B. Baruwati and S. V. Manorama, Org. Lett.,
2007, 9, 1419; (d) A. J. Amali and R. K. Rana, Green Chem., 2009,
11, 1781; (e) N. J. S. Costa, P. K. Kiyohara, A. L. Monteiro, Y. Copped,
K. Philippot and L. M. Rossi, J. Catal., 2010, 276, 382; ( f ) M. J. Jin
and D. H. Lee, Angew. Chem., Int. Ed., 2010, 49, 1119; (g) H. Q. Yang,
Y. W. Wang, Y. Qin, Y. Chong, Q. Yang, G. Li, L. Zhang and W. Li,
Green Chem., 2011, 13, 1352; (h) S. Zhou, M. Johnson and J. G. C.
Veinot, Chem. Commun., 2010, 46, 2411.
14 S. Shylesh, L. Wang and W. R. Thiel, Adv. Synth. Catal., 2010,
352, 425.
15 Q. W. Du, W. Zhang, H. Ma, J. Zheng, B. Zhou and Y. Q. Li,
Tetrahedron, 2012, 68, 3577.
16 (a) L. Zhang, P. H. Li, H. J. Li and L. Wang, Catal. Sci. Technol., 2012,
2, 1859; (b) P. H. Li, L. Wang, L. Zhang and G. W. Wang, Adv. Synth.
Catal., 2012, 354, 1307.
17 I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009.
18 (a) F. Amblard, J. H. Cho and R. F. Schinazi, Chem. Rev., 2009,
109, 4207; (b) C. Chu and R. Liu, Chem. Soc. Rev., 2011, 40, 2177.
19 A. K. Ganai, R. Bhardwaj, S. Hotha, S. S. Gupta and B. L. V. Prasad,
New J. Chem., 2010, 34, 2662.
1 For reviews, see: (a) N. Miyaura and A. Suzuki, Chem. Rev.,
1995, 95, 2457; (b) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz and
M. Lemaire, Chem. Rev., 2002, 102, 1359; (c) J. P. Corbet and
G. Mignani, Chem. Rev., 2006, 106, 2651; (d) L. Yin and J. Liebscher,
Chem. Rev., 2007, 107, 133; (e) R. Martin and S. L. Buchwald, Acc.
Chem. Res., 2008, 41, 1461; ( f ) A. Fihri, M. Bouhrara,
B. Nekoueishahraki, J. M. Basset and V. Polshettiwar, Chem. Soc.
Rev., 2011, 40, 5181.
2 (a) R. A. Forsch, S. F. Queener and A. Rosowsky, Bioorg. Med. Chem.
Lett., 2004, 14, 1811; (b) F. Leroux, ChemBioChem, 2004, 5, 644;
(c) S. Lightowler and M. Hird, Chem. Mater., 2005, 17, 5538;
(d) M. C. Kozlowski, B. J. Morgan and E. C. Linton, Chem. Soc. Rev.,
2009, 38, 3193; (e) A. Ogata, C. Furukawa, K. Sakurai, H. Iba, Y. Kitade
and Y. Ueno, Bioorg. Med. Chem. Lett., 2010, 20, 7299;
( f ) S. E. Dickson and C. M. Crudden, Chem. Commun., 2010, 46, 2100.
3 (a) A. F. Littke and G. C. Fu, Angew. Chem., Int. Ed., 2002, 41, 4176;
(b) I. Kondolff, H. Doucet and M. Santelli, Tetrahedron, 2004, 60, 3813;
(c) G. C. Fu, Acc. Chem. Res., 2008, 41, 1555; (d) A. N. Marziale,
D. Jantke, S. H. Faul, T. Reiner, E. Herdtweck and J. Eppinger, Green
Chem., 2011, 13, 169; (e) K. H. Chung, C. M. So, S. M. Wong,
C. H. Luk, Z. Zhou, C. P. Lau and F. Y. Kwong, Chem. Commun.,
2012, 48, 1967; ( f ) A. W. Fraser, J. E. Besaw, L. E. Hull and
M. C. Baird, Organometallics, 2012, 31, 2470.
´
4 (a) L. Botella and C. Najera, Angew. Chem., Int. Ed., 2002, 41, 179;
´
(b) L. Botella and C. Najera, J. Organomet. Chem., 2002, 663, 46;
´
(c) A. Corma, H. Garcıa and A. Leyva, J. Catal., 2006, 240, 87;
´
(d) E. Alacid and C. Najera, Org. Lett., 2008, 10, 5011; (e) E. Alacid
´
and C. Najera, J. Org. Chem., 2009, 74, 8191.
5 (a) O. Navarro, H. Kaur, P. Mahjoor and S. P. Nolan, J. Org. Chem.,
2004, 69, 3173; (b) A. E. Wang, J. H. Xie, L. X. Wang and Q. L. Zhou,
Tetrahedron, 2005, 61, 259; (c) E. A. B. Kantchev, C. J. brien and
M. G. Organ, Angew. Chem., Int. Ed., 2007, 46, 2768; (d) J. W. Ruan,
O. Saidi, J. A. Iggo and J. L. Xiao, J. Am. Chem. Soc., 2008, 130, 10510;
(e) A. Rahimi and A. Schmidt, Synlett, 2010, 1327; ( f ) C. Valente,
S. Çalimsiz, K. H. Hoi, D. Mallik, M. Sayah and M. G. Organ, Angew.
Chem., Int. Ed., 2012, 51, 3314.
6 (a) L. Bai and J. X. Wang, Adv. Synth. Catal., 2008, 350, 315;
´
(b) E. Alacid and C. Najera, J. Organomet. Chem., 2009, 694, 1658;
(c) S. M. Islam, P. Mondal, A. S. Roy, S. Mondal and D. Hossain,
Tetrahedron Lett., 2010, 51, 2067; (d) S. Ogasawara and S. Kato, J. Am.
Chem. Soc., 2010, 132, 4608; (e) J. Yang, P. Li and L. Wang, Synthesis,
2011, 1295; ( f ) R. U. Islam, M. J. Witcomb, M. S. Scurrell, E. van der
Lingen, W. V. Otterlo and K. Mallick, Catal. Sci. Technol., 2011,
1, 308; (g) D. Zhang, C. S. Zhou and R. H. Wang, Catal. Commun.,
2012, 22, 83; (h) M. C. Hong, M. C. Choi, Y. W. Chang, Y. Lee, J. Kim
and H. Rhee, Adv. Synth. Catal., 2012, 354, 1257.
7 (a) Y. Kitamura, A. Sakurai, T. Udzu, T. Maegawa, Y. Monguchi and
H. Sajiki, Tetrahedron, 2007, 63, 10596; (b) G. M. Scheuermann,
L. Rumi, P. Steurer, W. Bannwarth and R. Mu¨lhaupt, J. Am. Chem.
Soc., 2009, 131, 8262; (c) P. P. Zhang, X. X. Zhang, H. X. Sun,
R. H. Liu, B. Wang and Y. H. Lin, Tetrahedron Lett., 2009, 50, 4455.
8 (a) H. Q. Yang, X. J. Han, Z. C. Ma, R. Q. Wang, J. Liu and X. F. Ji,
Green Chem., 2010, 12, 441; (b) B. Karimi, D. Elhamifar, J. H. Clark
and A. J. Hunt, Chem.–Eur. J., 2010, 16, 8047; (c) D. H. Lee, J. Y. Jung
and M. J. Jin, Green Chem., 2010, 12, 2024; (d) W. Chen, P. Li and
L. Wang, Tetrahedron, 2011, 67, 318; (e) G. Li, H. Q. Yang, W. Li and
20 S. L. Jain, B. S. Rana, B. Singh, A. K. Sinha, A. Bhaumik, M. Nandi
and B. Sain, Green Chem., 2010, 12, 374.
21 G. F. Zhang, Y. Wang, X. Wen, C. R. Ding and Y. Li, Chem. Commun.,
2012, 48, 2979.
22 (a) Q. Zhang, J. Luo and Y. Y. Wei, Green Chem., 2010, 12, 2246;
(b) Q. Zhang, H. Su, J. Luo and Y. Y. Wei, Green Chem., 2012, 14, 201.
23 G. H. Lv, W. P. Mai, R. Jin and L. X. Gao, Synlett, 2008, 1418.
´
24 (a) S. Niembro, A. Shafir, A. Vallribera and R. Alibes, Org. Lett., 2008,
10, 3215; (b) R. Bernini, S. Cacchi, G. Fabrizi, G. Forte, F. Petrucci,
A. Prastaro, S. Niembro, A. Shafir and A. Vallribera, Green Chem.,
2010, 12, 150.
25 (a) N. Pinna, S. Grancharov, P. Beato, P. Bonville, M. Antonietti and
M. Niederberger, Chem. Mater., 2005, 17, 3044; (b) D. L. A. de Faria,
ˆ
S. Venancio Silva and M. T. De Oliveira, J. Raman Spectrosc., 1997,
28, 873; (c) L. Slavov, M. V. Abrashev, T. Merodiiska, Ch. Gelev,
R. E. Vandenberghe, I. Markova-Deneva and I. Nedkov, J. Magn.
Magn. Mater., 2010, 322, 1904.
c
This journal is The Royal Society of Chemistry 2013
Catal. Sci. Technol., 2013, 3, 235--243 243