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1
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57549099215
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Hassan, J.1
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T. Akiyama, J. Itoh, K. Yokota, and K. Fuchibe Angew. Chem., Int. Ed. 43 2004 1566 1568
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Akiyama, T.1
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0035753429
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G. Bringmann, C. Günther, M. Ochse, O. Schupp, and S. Tasler W. Herz, H. Falk, G.W. Kirby, R.E. Moore, Progress in the Chemistry of Organic Natural Products 2001 Springer Vienna Vol. 82, pp. 1-249
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Bringmann, G.1
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0038616412
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4544335033
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M.C. Willis, L.H. Powell, C.K. Claverie, and S. Watson Angew. Chem., Int. Ed. 43 2004 1249 1251
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34147143851
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Sawai, K.1
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70349786291
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Y. Uozumi, Y. Matsuura, T. Arakawa, and Y.M.A. Yamada Angew. Chem., Int. Ed. 48 2009 2708 2710
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Uozumi, Y.1
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Yamada, Y.M.A.4
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40
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55549114993
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Iwasawa, T.1
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Kawamura, Y.5
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45
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0034424538
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Müllen, K.7
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48
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79955479252
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The phosphonite 2, 3, and 4 were applied in the formation of tetra-ortho-substituted biaryl: a cross-coupling reaction with 2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane of 2,4,6-trimethylphenylboronic acid. However, any coupling adduct was not observed
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The phosphonite 2, 3, and 4 were applied in the formation of tetra-ortho-substituted biaryl: a cross-coupling reaction with 2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane of 2,4,6-trimethylphenylboronic acid. However, any coupling adduct was not observed.
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49
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79955477868
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note
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2P: C, 88.38; H, 5.44. Found: C, 88.28; H, 5.46.
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52
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34250816839
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J. Aydin, K.S. Kumar, M.J. Sayah, A. Olov, O.A. Wallner, and J.K. Szabó J. Org. Chem. 72 2007 4689 4697
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Aydin, J.1
Kumar, K.S.2
Sayah, M.J.3
Olov, A.4
Wallner, O.A.5
Szabó, J.K.6
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55
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37349073067
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F.R. Leroux, L. Bonnafoux, C. Heiss, F. Colobert, and D.A. Lanfranchi Adv. Synth. Catal. 349 2007 2705 2713
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(2007)
Adv. Synth. Catal.
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Leroux, F.R.1
Bonnafoux, L.2
Heiss, C.3
Colobert, F.4
Lanfranchi, D.A.5
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57
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47549111892
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T. Iwasawa, T. Kamei, K. Hama, Y. Nishimoto, M. Nishiuchi, and Y. Kawamura Tetrahedron Lett. 49 2008 5244 5246
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(2008)
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Iwasawa, T.1
Kamei, T.2
Hama, K.3
Nishimoto, Y.4
Nishiuchi, M.5
Kawamura, Y.6
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61
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79955471221
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note
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3: C, 75.53; H, 6.71. Found: C, 75.52; H, 6.75.
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63
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79955465237
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1H NMR data of a biaryl bearing axial chirality (R)
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1H NMR data of a biaryl bearing axial chirality (R).
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64
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79955463013
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The biaryl product in entries 10 and 11 was purified by recrystallization one time to remove small amounts of unclear byproducts
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The biaryl product in entries 10 and 11 was purified by recrystallization one time to remove small amounts of unclear byproducts.
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65
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79955483858
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Unfortunately, the derivatives from the cross-coupling reactions of 2-chrolo-3-methoxy benzonitrile 9 with ortho-tolylboronic acid 8, ortho-methoxyphenlylboronic acid 10, and ortho-formylphenylboronic acid did not have enough rotation barriers to maintain the axial chirality. The spectra of HPLC indicate that these bialys are racemic compounds even at 298 K
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Unfortunately, the derivatives from the cross-coupling reactions of 2-chrolo-3-methoxy benzonitrile 9 with ortho-tolylboronic acid 8, ortho-methoxyphenlylboronic acid 10, and ortho-formylphenylboronic acid did not have enough rotation barriers to maintain the axial chirality. The spectra of HPLC indicate that these bialys are racemic compounds even at 298 K.
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