Beilstein Journal of Organic Chemistry 2009, 5, No. 16.
7. Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366–374.
fast mixing in microflow systems. Electrophiles was introduced
on one of the aromatic rings with high selectivity. Sequential
introduction of two electrophiles by repeating the sequence
have also been achieved using the integrated microflow
systems. Unsymmetrically substituted biaryls were obtained in
high selectivity. The results obtained in this study speak well
for the potential of integrated microflow systems in multi-step
synthesis in flash chemistry [59-61], and the method adds a new
dimension to the synthesis of unsymmetrically substituted
biaryls.
8. Liebscher, J.; Yin, L. Chem. Rev. 2007, 107, 133–173.
9. Doucet, H.; Hierso, J. C. Angew. Chem., Int. Ed. 2007, 46, 834–871.
10.Beak, P.; Liu, C. Tetrahedron Lett. 1994, 20, 5999–6004.
11.Dolman, S. J.; Gosselin, F.; O’Shea, P. D.; Davies, I. W. Tetrahedron
12.Kliś, T.; Servatowski, J. Tetrahedron Lett. 2007, 48, 1169–1173.
13.Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.;
Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58,
14.Jähnisch, K.; Hessel, V.; Löwe, H.; Baerns, M. Angew. Chem., Int. Ed.
Supporting Information
Experimental procedures and full spectroscopic data for all
new compounds are provided as supporting information.
15.Doku, G. N.; Verboom, W.; Reinhoudt, D. N.; van den Berg, A.
16.Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett.
Supporting Information File 1
17.Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.;
Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305–1308.
Experimental procedures for compounds 1–52.
18.Wu, T.; Mei, Y.; Cabrai, J. T.; Xu, C.; Beers, K. L. J. Am. Chem. Soc.
Supporting Information File 2
1H NMR spectra and 13C NMR spectra of compounds 4, 5,
9–16, 19, 22–26, 31–35, 39.
19.Ducry, L.; Roberge, D. M. Angew. Chem., Int. Ed. 2005, 44,
20.Iwasaki, T.; Yoshida, J. Macromolecules 2005, 38, 1159–1163.
21.Lee, C. C.; Sui, G. D.; Elizarov, A.; Shu, C. Y. J.; Shin, Y. S.;
Dooley, A. N.; Huang, J.; Daridon, A.; Wyatt, P.; Stout, D.; Kolb, H. C.;
Witte, O. N.; Satyamurthy, N.; Heath, J. R.; Phelps, M. E.;
Quake, S. R.; Tseng, H. R. Science 2005, 310, 1793–1796.
Supporting Information File 3
1H NMR spectra and 13C NMR spectra of compounds 41,
42, 46, 48–52.
22.He, P.; Watts, P.; Marken, F.; Haswell, S. J. Angew. Chem., Int. Ed.
23.Uozumi, Y.; Yamada, Y.; Beppu, T.; Fukuyama, N.; Ueno, M.;
Kitamori, T. J. Am. Chem. Soc. 2006, 128, 15994–15995.
24.Belder, D.; Ludwig, M.; Wang, L. W.; Reetz, M. T.
Angew. Chem., Int. Ed. 2006, 45, 2463–2466.
Acknowledgments
This work was financially supported in part by a Grant-in-Aid
for Scientific Research from the Japan Society for the Promo-
tion of Science and NEDO projects.
25.Tanaka, K.; Motomatsu, S.; Koyama, K.; Tanaka, S.; Fukase, K.
26.Sahoo, H. R.; Kralj, J. G.; Jensen, K. F. Angew. Chem., Int. Ed. 2007,
28.Rys, P. Angew. Chem., Int. Ed. 1977, 12, 807–817.
References
1. Cepanec, I. Synthesis of Biaryls; ELSEVIER, 2004.
2. Negishi, E. Handbook of Organopalladium Chemistry for Organic
Synthesis; Wiley-Interscience: New York, 2002.
3. Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953–956.
29.Suga, S.; Nagaki, A.; Yoshida, J. Chem. Commun. 2003, 354–355.
30.Suga, S.; Nagaki, A.; Tsutsui, Y.; Yoshida, J. Org. Lett. 2003, 5,
31.Suga, S.; Tsutsui, Y.; Nagaki, A.; Yoshida, J. Bull. Chem. Soc. Jpn.
4. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234–245.
32.Nagaki, A.; Togai, M.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J.
33.Yoshida, J.; Nagaki, A.; Iwasaki, T.; Suga, S. Chem. Eng. Technol.
5. Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453–3516.
6. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873–2920.
Page 10 of 11
(page number not for citation purposes)