Y. Monguchi et al. / Tetrahedron 67 (2011) 8628e8634
8633
(CDCl3):
d
55.3, 110.0, 114.5, 119.0, 127.0, 128.3, 131.4, 132.5, 145.1,
Scientific Research Grant from the Japan Science Society, the Re-
search for Promoting Technological Seeds Program in 2007 and
2009 from the Japan Science and Technology Agency (JST), and
a Grant-in Aid for Scientific Research (No. 21590015) from the
Ministry of Education, Culture, Science, Sports, Science and Tech-
nology, Japan, and Gifu Pharmaceutical University.
160.2. MS (EI) m/z (%): 209 (Mþ, 100), 194 (31), 166 (44).
4.4.9. Ethyl 40-methoxy-1,10-biphenyl-4-carboxylate (Table 6, entry
10)40
.
1H NMR (CDCl3):
d
1.40 (3H, t, J¼7.2 Hz), 3.84 (3H, s), 4.39
(2H, q, J¼7.2 Hz), 6.98 (2H, d, J¼8.2 Hz), 7.55 (2H, d, J¼8.2 Hz), 7.60
(2H, d, J¼8.2 Hz), 8.07 (2H, d, J¼8.2 Hz); 13C NMR (CDCl3):
d 14.3,
55.3, 60.8, 114.3, 126.4, 128.3, 128.6, 130.0, 132.4, 145.0, 159.8, 166.5.
References and notes
MS (EI) m/z (%): 256 (Mþ, 100), 211 (56).
1. Anastas, P.; Warner, J. Green Chemistry. Theory and Practice; Oxford University:
Oxford, 1998.
4.4.10. 4-Hydroxy-40-methoxy-1,10-biphenyl (Table 6, entry 11). 1H
2. (a) Solvent-free Organic Synthesis, 2nd ed.; Tanaka, K., Ed.; WILEY-VCH: Wein-
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3. (a) Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; WILEY-
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4. Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic
Synthesis; Wiley-VCH: New York, NY, 2001.
5. (a) Seki, M. J. Syn. Org. Chem. Jpn. 2006, 64, 853e866; (b) Seki, M. Synthesis
2006, 2975e2992; (c) Felpin, F.-X.; Ayad, T.; Mitra, S. Eur. J. Org. Chem. 2006,
2679e2690.
6. (a) Conlon, D. A.; Pipik, B.; Ferdinand, S.; LeBlond, C. R.; Sowa, J. R., Jr.; Izzo, B.;
Collins, P.; Ho, G.-J.; Williams, J. M.; Shi, Y.-J.; Sun, Y. Adv. Synth. Catal. 2003, 345,
931e935; (b) Tagata, T.; Nishida, M. J. Org. Chem. 2003, 68, 9412e9415; (c)
Arcadi, A.; Cerichelli, G.; Chiarini, M.; Correa, M.; Zorzan, D. Eur. J. Org. Chem.
NMR (acetone-d6):
d
3.79 (3H, s), 6.92 (2H, d, J¼8.8 Hz), 6.95 (2H, d,
J¼8.8 Hz), 7.44 (2H, d, J¼8.6 Hz), 7.49 (2H, d, J¼8.6 Hz), 8.38(1H, s); 13C
NMR (acetone-d6): d 55.5, 114.9,116.5,128.1, 128.3, 132.9, 134.2, 157.3,
159.6. The NMR spectra were identical with those of the commercial
products from TCI. MS (EI) m/z (%): 200 (Mþ, 100), 185 (52).
4.4.11. 4-Amino-40-methoxybiphenyl (Table 6, entry 12)41. 1H NMR
(CDCl3):
d
3.68 (2H, br s), 3.81 (3H, s), 6.72 (2H, d, J¼8.2 Hz), 6.93
(2H, d, J¼8.5 Hz), 7.35 (2H, d, J¼8.2 Hz), 7.44 (2H, d, J¼8.5 Hz); 13C
NMR (CDCl3):
d 29.7, 55.3, 114.1, 115.4, 127.4, 131.3, 133.8, 145.3,
158.4. MS (EI) m/z (%): 199 (Mþ, 100), 184 (84).
4.4.12. 2-Methyl-40-methoxy-1,10-biphenyl (Table 6, entry 13)7d 1H
.
NMR (CDCl3):
d
2.27 (3H, s), 3.84 (3H, s), 6.94 (2H, d, J¼8.2 Hz),
7.21e7.26 (6H, m); 13C NMR (CDCl3):
d 20.5, 55.2, 113.5, 125.7, 126.9,
129.9, 130.2, 134.4, 135.5, 141.5, 158.5. MS (EI) m/z (%): 198 (Mþ,
2003, 4080e4086; (d) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118ˇ e124;
ꢀ
(e) Cravotto, G.; Beggiato, M.; Penoni, A.; Palmisano, G.; Tollari, S.; Leveque, J.-
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J. R., Jr. Tetrahedron 2007, 63, 12646e12654; (g) Jiang, J.-Z.; Cai, C. J. Dispersion
Sci. Technol. 2008, 29, 453e456; (h) Batail, N.; Bendjeriou, A.; Lomberget, T.;
Barret, R.; Dufaud, V.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 2055e2062.
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K. J. Chem. Res. 2004, 593e595; Erratum: J. Chem. Res. 2005, 344; (b) Sajiki, H.;
Kurita, T.; Kozaki, A.; Zhang, G.; Kitamura, Y.; Maegawa, T.; Hirota, K. Synthesis
2005, 537e542; Erratum: Synthesis 2005, 852; (c) Maegawa, T.; Kitamura, Y.;
Sako, S.; Udzu, T.; Sakurai, A.; Tanaka, A.; Kobayashi, Y.; Endo, K.; Bora, U.;
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5937e5943; (d) Kitamura, Y.; Sakurai, A.; Udzu, T.; Maegawa, T.; Monguchi, Y.;
Sajiki, H. Tetrahedron 2007, 63, 10596e10602; (e) Kitamura, Y.; Sako, S.; Udzu,
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100), 183 (25).
4.4.13. 4-Methoxy-1,10-biphenyl (Table 6, entry 14). 1H NMR
(CDCl3):
7.39 (2H, t, J¼7.7 Hz), 7.51 (2H, d, J¼8.7 Hz), 7.54 (2H, d, J¼7.2 Hz);
13C NMR (CDCl3):
55.3, 114.2, 126.6, 126.7, 128.1, 128.7, 133.7, 140.8,
d
3.81 (3H, s), 6.96 (2H, d, J¼8.7 Hz), 7.28 (1H, t, J¼7.7 Hz),
d
159.1. The NMR spectra were identical with those of the commercial
products from SigmaeAldrich. MS (EI) m/z (%): 184 (Mþ, 100), 169
(36), 141 (45).
4.4.14. 1-(4-Methoxyphenyl)naphthalene (Table 6, entry 15)42
.
1H
NMR (CDCl3):
d
3.86 (3H, s), 7.01 (2H, d, J¼8.8 Hz), 7.38e7.50 (6H,
m), 7.81 (1H, d, J¼8.3 Hz), 7.87 (1H, d, J¼7.8 Hz), 7.92 (1H, d,
8. (a) Sajiki, H.; Zhang, G.; Kitamura, Y.; Maegawa, T.; Hirota, K. Synlett 2005,
619e622; Erratum: Synlett 2005, 1046; (b) Mori, S.; Yanase, T.; Aoyagi, S.;
Monguchi, Y.; Maegawa, T.; Sajiki, H. Chem.dEur. J. 2008, 14, 6994e6999.
9. Monguchi, Y.; Kitamoto, K.; Ikawa, T.; Maegawa, T.; Sajiki, H. Adv. Synth. Catal.
2008, 350, 2767e2777.
J¼8.3 Hz); 13C NMR (CDCl3):
d 55.3, 113.7, 125.4, 125.7, 125.9, 126.0,
126.9, 127.3, 128.2, 131.1, 131.8, 133.1, 133.8, 139.9, 158.9. MS (EI) m/z
(%): 234 (Mþ, 100), 219 (24).
10. (a) Lamartine, R.; Perrin, R. Mol. Cryst. Liq. Cryst. 1983, 96, 57e69; (b) Kaup, G.;
Matties, D. Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt. 1988, 161, 119e143; (c) Sabra, F.;
Bassus, J.; Lamartine, R. Mol. Cryst. Liq. Cryst. 1990, 186, 69e72; (d) Sabra, F.;
Lamartine, R. New J. Chem. 1992, 16, 1043e1048; (e) Sabra, F.; Lamartine, R. New
J. Chem. 1992, 16, 1049e1051; (f) Kitamura, T.; Harada, T.; Osawa, T. In Spillover
and Migration of Surface Species on Catalysts; Li, C., Xin, Q., Eds.; Elsevier: Am-
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Kitamura, T.; Harada, T. Green Chem. 2001, 3, 252e256.
4.4.15. 4-Acetyl-40-hydroxy-1,10-biphenyl (Table 6, entry 16)43
NMR (CDCl3):
2.64 (3H, s), 5.06 (1H, br s), 6.95 (2H, d, J¼8.4 Hz),
7.54 (2H, d, J¼8.4 Hz), 7.64 (2H, d, J¼8.4 Hz), 8.02 (2H, d, J¼8.4 Hz);
.
1H
d
13C NMR (CDCl3):
d 26.6, 115.9, 126.6, 128.6, 129.0, 132.5, 135.3,
145.3, 155.9. 197.8. MS (EI) m/z (%): 212 (Mþ, 57), 197 (100).
4.4.16. 4-Acetyl-40-methoxy-1,10-biphenyl (Table 6, entry 17)7c 1H
.
11. (a) Hermans, S.; Raja, R.; Thomas, J. M.; Johnson, B. F. G.; Sankar, G.; Gleeson, D.
Angew. Chem. 2001, 113, 1251e1255; Angew. Chem., Int. Ed. 2001, 40, 1211e1215;
(b) Adams, R. D.; Boswell, E. M.; Captain, B.; Hungria, A. B.; Midgley, P. A.; Raja,
R.; Thomas, J. M. Angew. Chem. 2007, 119, 8330e8333; Angew. Chem., Int. Ed.
2007, 46, 8182e8185.
NMR (CDCl3):
d
2.63 (3H, s), 3.86 (3H, s), 7.00 (2H, d, J¼8.8 Hz), 7.58
(2H, d, J¼8.8 Hz), 7.64 (2H, d, J¼8.4 Hz), 8.01 (2H, d, J¼8.4 Hz); 13C
NMR (CDCl3):
d 26.6, 55.4, 114.4, 126.6, 128.4, 128.9, 132.2, 135.3,
145.4, 159.9. 197.9. MS (EI) m/z (%): 226 (Mþ, 58), 211 (100).
€
12. Zahmakıran, M.; Tonbul, Y.; Ozkar, S. J. Am. Chem. Soc. 2010, 132, 6541e6549.
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Chem. 2000, 2, 120e122; (b) Melucci, M.; Barbarella, G.; Sotgiu, G. J. Org. Chem.
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4.4.17. 2-(4-Methoxyphenyl)pyridine
(CDCl3):
(Scheme
1)7e 1H NMR
.
d
3.83 (3H, s), 6.98 (2H, d, J¼6.8 Hz), 7.14 (1H, ddd, J¼1.5,
4.9, 6.8 Hz), 7.64 (1H, m), 7.68 (1H, m), 7.94 (2H, d, J¼8.8 Hz), 8.64
(1H, m); 13C NMR (CDCl3):
d 55.3, 114.1, 119.7, 121.3, 128.1, 132.0,
136.6, 149.5, 157.1, 160.4. MS (EI) m/z (%): 185 (Mþ, 100), 170 (24).
Acknowledgements
We are grateful to the N.E. Chemcat Corporation for the 10% Pd/C
gift. This work was partly financially supported by a Sasakawa