Suzuki–Miyaura Cross-Coupling Reactions in Solkane365/227/Ethanol
[7]
For recent examples, see: a) S. S. Soomro, C. Röhlich, K.
Köhler, Adv. Synth. Catal. 2011, 353, 767–775; b) N. Liu, C.
Liu, B. Yan, Z.-L. Jin, Appl. Organomet. Chem. 2011, 25, 168–
172; c) P. Das, C. Sarmah, A. Tairai, U. Bora, Appl. Organomet.
Chem. 2011, 25, 283–288; d) Y.-P. Yu, T.-J. Hu, X.-R. Chen,
K.-L. Xu, J.-L. Zhang, J. Huang, Chem. Commun. 2011, 47,
3592–3594; e) B. Karimi, P. F. Akhavan, Chem. Commun. 2011,
47, 7686–7688; f) A. Ohtaka, Y. Kono, T. Teratani, S. Fujii, S.
Matsuzawa, Y. Nakamura, R. Nomura, Catal. Lett. 2011, 141,
1097–1103; g) S. Dastgir, K. S. Coleman, M. L. H. Green, Dal-
ton Trans. 2011, 40, 661–672; h) A. Fihri, D. Luart, C. Len, A.
Solhy, C. Chevrin, V. Polshettiwar, Dalton Trans. 2011, 40,
3116–3121; i) A. N. Marziale, D. Jantke, S. H. Faul, T. Reiner,
E. Herdtweck, J. Eppinger, Green Chem. 2011, 13, 169–177; j)
L.-Y. Li, J.-Y. Wang, C.-S. Zhou, R.-H. Wang, M.-C. Hong,
Green Chem. 2011, 13, 2071–2077; k) C.-S. Zhou, J.-Y. Wang,
L.-Y. Li, R.-H. Wang, M.-C. Hong, Green Chem. 2011, 13,
2100–2106; l) B. Karimi, P. F. Akhavan, Inorg. Chem. 2011, 50,
6063–6072; m) A. Ohtaka, T. Teratani, R. Fujii, K. Ikeshita,
T. Kawashima, K. Tatsumi, O. Shimomura, R. Nomura, J. Org.
Chem. 2011, 76, 4052–4060; n) Y.-Q. Tang, H. Lv, J.-M. Lu,
L.-X. Shao, J. Organomet. Chem. 2011, 696, 2576–2579; o) N.
Liu, C. Liu, Z.-L. Jin, J. Organomet. Chem. 2011, 696, 2641–
2647; p) F. Godoy, C. Segarra, M. Poyatos, E. Peris, Organome-
tallics 2011, 30, 684–688; q) L. Lin, Y.-C. Li, S.-B. Zhang, S.-
H. Li, Synlett 2011, 1779–1783.
Supporting Information (see footnote on the first page of this arti-
cle): Experimental procedures and analytical data for compounds
3a–x, 5a, and 5b, including copies of the 1H and 13C NMR spectra.
Acknowledgments
This study was financially supported in part by Grants-in-Aid for
Scientific Research from the Ministry of Education, Culture,
Sports, Science and Technology (21390030, 22106515, Project No.
2105: Organic Synthesis Based on Reaction Integration). We thank
Dr. Max Braun, Solvay Fluor GmbH for the generous gift of Solk-
ane365/227. We also thank the Asahi Glass Foundation for finan-
cial support.
[1] For reviews, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995,
95, 2457–2483; b) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz,
M. Lemaire, Chem. Rev. 2002, 102, 1359–1469; c) A. F. Littke,
G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int.
Ed. 2002, 41, 4176–4211; d) S. Kotha, K. Lahiri, D. Kashinath,
Tetrahedron 2002, 58, 9633–9695; e) J.-P. Corbet, G. Mignani,
Chem. Rev. 2006, 106, 2651–2710; f) L.-X. Yin, J. Liebscher,
Chem. Rev. 2007, 107, 133–173; g) A. Suzuki, Angew. Chem.
Int. Ed. 2011, 50, 6722–6737.
[2] For reviews, see: a) P. Lloyd-Williams, E. Giralt, Chem. Soc.
Rev. 2001, 30, 145–157; b) M. Sasaki, H. Fuwa, Synlett 2004,
1851–1874; c) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew.
Chem. 2005, 117, 4516; Angew. Chem. Int. Ed. 2005, 44, 4442–
4489; d) O. Baudoin, Eur. J. Org. Chem. 2005, 4223–4229.
[3] For recent examples, see: a) G. Viault, D. Grée, S. Das, J. S.
Yadav, R. Grée, Eur. J. Org. Chem. 2011, 1233–1241; b) S. Ki-
mura, S. Kobayashi, T. Kumamoto, A. Akagi, N. Sato, T. Ishi-
kawa, Helv. Chim. Acta 2011, 94, 578–591; c) H. A. Ioannidou,
A. Martin, A. Gollner, P. A. Koutentis, J. Org. Chem. 2011, 76,
5113–5122; d) J. Deguchi, T. Hirahara, S. Oshimi, Y. Hirasawa,
W. Ekasari, O. Shirota, T. Honda, H. Morita, Org. Lett. 2011,
13, 4344–4347; e) W. Phakhodee, M. Toyoda, C.-M. Chou, N.
Khunnawutmanotham, M. Isobe, Tetrahedron 2011, 67, 1150–
1157; f) Y. Ishihara, S. Azuma, T. Choshi, K. Kohno, K. Ono,
H. Tsutsumi, T. Ishizu, S. Hibino, Tetrahedron 2011, 67, 1320–
1333.
[4] For recent examples, see: a) J.-K. Lee, M. C. Gwinner, R. Ber-
ger, C. Newby, R. Zentel, R. H. Friend, H. Sirringhaus, C. K.
Ober, J. Am. Chem. Soc. 2011, 133, 9949–9951; b) R. K. Cheed-
arala, G.-H. Kim, S. Cho, J. Lee, J. Kim, H.-K. Song, J. Y.
Kim, C. Yang, J. Mater. Chem. 2011, 21, 843–850; c) C. W.
Keyworth, K. L. Chan, J. G. Labram, T. D. Anthopoulos, S. E.
Watkins, M. McKiernan, A. J. P. White, A. B. Holmes, C. K.
Williams, J. Mater. Chem. 2011, 21, 11800–11814; d) Q. Chen,
J.-X. Wang, F. Yang, D. Zhou, N. Bian, X.-J. Zhang, C.-G.
Yan, B.-H. Han, J. Mater. Chem. 2011, 21, 13554–13560; e) R.
Verduzco, I. Botiz, D. L. Pickel, S. M. Kilbey II, K. Hong, E.
Dimasi, S. B. Darling, Macromolecules 2011, 44, 530–539; f) K.
Zhang, B. Tieke, Macromolecules 2011, 44, 4596–4599; g) R.
Stalder, J. Mei, J. Subbiah, C. Grand, L. A. Estrada, F. So, J. R.
Reynolds, Macromolecules 2011, 44, 6303–6310.
[5] For reviews, see: a) L. Bai, J.-X. Wang, Curr. Org. Chem. 2005,
9, 535–553; b) F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron
2008, 64, 3047–3101; c) V. Polshettiwar, A. Decottignies, C.
Len, A. Fihri, ChemSusChem 2010, 3, 502–522; d) A. Fihri, M.
Bouhrara, B. Nekoueishahraki, J.-M. Basset, V. Polshettiwar,
Chem. Soc. Rev. 2011, 40, 5181–5203.
[8]
For recent examples, see: a) H. Nowothnick, J. Blum, R.
Schomäcker, Angew. Chem. Int. Ed. 2011, 50, 1918–1921; b) C.
Sarmah, M. Borah, P. Das, Appl. Organomet. Chem. 2011, 25,
552–558; c) L. Wan, C. Cai, Catal. Lett. 2011, 141, 839–843;
d) A. Modak, J. Mondal, M. Sasidharan, A. Bhaumik, Green
Chem. 2011, 13, 1317–1331; e) J. A. Weeden, R. Huang, K. D.
Galloway, P. W. Gingrich, B. J. Frost, Molecules 2011, 16,
6215–6231; f) C. Liu, Q.-J. Ni, P.-P. Hu, J.-S. Qiu, Org. Biomol.
Chem. 2011, 9, 1054–1060; g) J.-Y. Wang, G.-H. Song, Y.-Q.
Peng, Tetrahedron Lett. 2011, 52, 1477–1480.
[9]
a) C. J. Mathews, P. J. Smith, T. Welton, Chem. Commun. 2000,
1249–1250; b) G. Zou, Z.-Y. Wang, J.-R. Zhu, J. Tang, M.-Y.
He, J. Mol. Catal. A 2003, 206, 193–198; c) F. McLachlan,
C. J. Mathews, P. J. Smith, T. Welton, Organometallics 2003, 22,
5350–5357; d) D.-B. Zhao, Z.-F. Fei, T. J. Geldbach, R. Scopel-
liti, P. J. Dyson, J. Am. Chem. Soc. 2004, 126, 15876–15882; e)
V. Calò, A. Nacci, A. Monopoli, F. Montingelli, J. Org. Chem.
2005, 70, 6040–6044; f) B.-W. Xin, Y.-H. Zhang, L.-F. Liu, Y.-
G. Wang, Synlett 2005, 3083–3086; g) C.-H. Yang, C.-C. Tai,
Y.-T. Huang, I.-W. Sun, Tetrahedron 2005, 61, 4857–4861; h)
H.-T. Wong, S.-J. Han, A. G. Livingston, Chem. Eng. Sci. 2006,
61, 1338–1341; i) R.-H. Wang, B. Twamley, J. M. Shreeve, J.
Org. Chem. 2006, 71, 426–429; j) R.-H. Wang, M. M. Piekar-
ski, J. M. Shreeve, Org. Biomol. Chem. 2006, 4, 1878–1886; k)
F. Fernández, B. Cordero, J. Durand, G. Muller, F. Malbosc,
Y. Kihn, E. Teuma, M. Gómez, Dalton Trans. 2007, 5572–5581;
l) X. Yang, Z.-F. Fei, T. J. Geldbach, A. D. Phillips, C. G. Hart-
inger, Y.-D. Li, P. J. Dyson, Organometallics 2008, 27, 3971–
3977; m) M. Lombardo, M. Chiarucci, C. Trombini, Green
Chem. 2009, 11, 574–579; n) M. H. G. Prechtl, J. D. Scholten,
J. Dupont, Molecules 2010, 15, 3441–3461; o) A. Papagni, C.
Trombini, M. Lombardo, S. Bergantin, A. Chams, M. Chia-
rucci, L. Miozzo, M. Parravicini, Organometallics 2011, 30,
4325–4329; p) M. V. Escárcega-Bobadilla, E. Teuma, A. M.
Masdeu-Bultó, M. Gómez, Tetrahedron 2011, 67, 421–428; q)
K. L. S. Castro, P. G. Lima, L. S. M. Miranda, R. O. M. A.
Souza, Tetrahedron Lett. 2011, 52, 4168–4171.
[10]
[11]
a) C. J. Mathews, P. J. Smith, T. Welton, J. Mol. Catal. A 2004,
214, 27–32; b) S. Liu, T. Fukuyama, M. Sato, I. Ryu, Synlett
2004, 1814–1816; c) J.-C. Xiao, J. M. Shreeve, J. Org. Chem.
2005, 70, 3072–3078; d) N. Yan, X. Yang, Z.-F. Fei, Y.-D. Li,
Y. Kou, P. J. Dyson, Organometallics 2009, 28, 937–939.
a) R. Rajagopal, D. V. Jarikote, K. V. Srinivasan, Chem. Com-
mun. 2002, 616–617; b) J. McNulty, A. Capretta, J. Wilson, J.
[6] a) P. T. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35,
686–694; b) M. Doble, A. K. Kruthiventi in Green Chemistry
and Processes, Academic Press, Burlington, MA, 2007; c) V. K.
Ahluwalia in Green Chemistry: Environmentally Benign Reac-
tions, CRC, Taylor & Francis, Boca Raton, FL, 2008.
Eur. J. Org. Chem. 2012, 1504–1508
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
1507