D. Saha et al. / Tetrahedron 69 (2013) 3951e3960
3959
(s, 3H); 13C NMR (75 MHz, CDCl3, ppm)
129.0, 129.0, 128.3, 127.3, 127.3, 26.7.
d
197.8, 145.8, 139.9, 135.9,
128.5 (q, J¼31.9 Hz), 125.5 (q, J¼3.5 Hz), 124.5 (q, J¼269.9 Hz), 114.2,
55.4, 41.0.
4.1.15. 4-Nitrobiphenyl (4b).5a 1H NMR (300 MHz, CDCl3, ppm)
4.1.27. 1-(4-Fluorobenzyl)-4-methoxybenzene
(4n).11 1H
NMR
d
8.30 (d, J¼8.7 Hz, 2H), 7.74 (d, J¼8.7 Hz, 2H), 7.63 (dd, J¼7.8, 1.4 Hz,
(300 MHz, CDCl3)
d
7.18e7.10 (m, 4H), 6.99 (t, J¼8.7 Hz, 2H), 6.87 (d,
2H), 7.53e7.42 (m, 3H); 13C NMR (75 MHz, CDCl3, ppm)
d
147.7,
J¼8.6 Hz, 2H), 3.92 (s, 2H), 3.81 (s, 3H); 13C NMR (75 MHz, CDCl3)
147.2, 138.9, 129.3, 129.0, 127.9, 127.5, 124.2.
d
161.5 (d, J¼242.2 Hz), 158.2, 137.4 (d, J¼3.0 Hz), 133.2, 130.3 (d,
J¼7.8 Hz), 129.9, 115.3 (d, J¼21.1 Hz), 114.1, 55.4, 40.3.
4.1.16. 4-Cyanobiphenyl (4c).5a 1H NMR (300 MHz, CDCl3, ppm)
d
7.74e7.67 (m, 4H), 7.59 (dd, J¼8.0, 1.6 Hz, 2H), 7.49e7.45 (m, 3H);
4.1.28. 1-(3-Chlorobenzyl)-4-methoxybenzene
(4o).11 1H
NMR
13C NMR (75 MHz, CDCl3, ppm)
127.8, 127.3, 119.0, 111.0.
d
145.7, 139.3, 132.7, 129.2, 128.8,
(300 MHz, CDCl3) d 7.26e7.24 (m, 3H), 7.17e7.11 (m, 3H), 6.91 (d,
J¼8.2 Hz, 2H), 3.95 (s, 2H), 3.84 (s, 3H); 13C NMR (75 MHz, CDCl3)
d
158.3, 143.8, 134.3, 132.4, 130.0, 129.8, 129.0, 127.1, 126.3, 114.1,
4.1.17. 4-Methoxybiphenyl (4d).5a 1H NMR (300 MHz, CDCl3, ppm)
55.3, 40.8.
d
7.48e7.43 (m, 4H), 7.32 (t, J¼7.2 Hz, 2H), 7.21 (t, J¼7.2 Hz, 1H), 6.89
(d, J¼8.8 Hz, 2H), 3.75 (s, 3H); 13C NMR (75 MHz, CDCl3, ppm)
4.1.29. 1-(4-Methoxyphenyl)naphthalene (4p).14 1H NMR (500 MHz,
d
159.3, 140.9, 133.9, 128.9, 128.3, 126.9, 126.8, 114.3, 55.5.
CDCl3)
d
7.97e7.91 (m, 2H), 7.86 (d, J¼8.5 Hz, 1H), 7.55e7.49 (m,
2H), 7.46e7.43 (m, 4H), 7.06 (d, J¼8.5 Hz, 2H), 3.92 (s, 3H); 13C NMR
4.1.18. 3-Methoxy-40-methylbiphenyl (4e).12 1H NMR (300 MHz,
CDCl3, ppm)
7.51 (d, J¼8.1 Hz, 2H), 7.36 (t, J¼7.9 Hz, 1H), 7.26 (d,
J¼7.9 Hz, 2H), 7.19e7.13 (m, 2H), 6.90 (d, J¼6.9 Hz, 1H), 3.88 (s, 3H),
2.41 (s, 3H); 13C NMR (75 MHz, CDCl3, ppm)
160.1, 142.9, 138.4,
(125 MHz, CDCl3) d 159.1, 140.1, 134.0, 133.3, 132.0, 131.3, 128.4,
d
127.5, 127.0, 126.2, 126.1, 125.8, 125.5, 113.9, 55.5.
d
4.1.30. 1-(2-Methoxyphenyl)naphthalene (4q).15 1H NMR (500 MHz,
137.4, 129.8, 129.6, 127.2, 119.7, 112.9, 112.5, 55.4, 21.2.
CDCl3)
1H), 7.50e7.39 (m, 4H), 7.32 (d, J¼8.5 Hz, 1H), 7.13e7.07 (m, 2H),
3.72 (s, 3H); 13C NMR (125 MHz, CDCl3)
157.4, 137.1, 133.6, 132.3,
d
7.92e7.88 (m, 2H), 7.62 (d, J¼8.5 Hz, 1H), 7.56 (t, J¼7.0 Hz,
4.1.19. 4-Methylbiphenyl (4f).4e 1H NMR (300 MHz, CDCl3, ppm)
d
d
7.60 (d, J¼7.6 Hz, 2H), 7.53 (d, J¼7.0 Hz, 2H), 7.44 (t, J¼7.2 Hz, 2H),
132.1,129.7,129.1,128.3,127.8,127.4,126.6,125.8,125.7,125.5,120.7,
111.2, 55.7.
7.35 (d, J¼6.7 Hz, 1H), 7.26 (d, J¼7.5 Hz, 2H), 2.41 (s, 3H); 13C NMR
(75 MHz, CDCl3, ppm)
21.3.
d 141.3, 138.5, 137.2, 129.7, 128.9, 127.2, 127.2,
4.1.31. 40-Methoxy-2,4,6-trimethylbiphenyl
(4r).16 1H
NMR
(500 MHz, CDCl3)
d
7.08 (d, J¼8.5 Hz, 2H), 6.99e6.96 (m, 4H), 3.88
4.1.20. 2-Nitrobiphenyl (4g).5a 1H NMR (300 MHz, CDCl3)
d
7.85 (d,
(s, 3H), 2.35 (s, 3H), 2.04 (s, 6H); 13C NMR (125 MHz, CDCl3)
138.8, 136.5, 133.5, 130.5, 128.2, 113.9, 55.3, 21.1, 20.9.
d 158.3,
J¼8.0 Hz, 1H), 7.62e7.59 (m, 1H), 7.48e7.41 (m, 5H), 7.35e7.32 (m,
2H); 13C NMR (75 MHz, CDCl3)
128.7, 128.3, 128.2, 127.9, 124.1.
d 149.3, 137.4, 136.3, 132.4, 132.0,
Acknowledgements
4.1.21. 1-Acetyl-4-phenylnaphthalene (4h).13 1H NMR (300 MHz,
CDCl3, ppm)
8.10 (d, J¼8.3 Hz, 2H), 7.94e7.84 (m, 3H), 7.63e7.42
(m, 6H), 2.69 (s, 3H); 13C NMR (75 MHz, CDCl3, ppm)
198.0, 145.9,
139.1, 136.1, 134.0, 131.3, 130.4, 128.6, 128.5, 127.1, 126.5, 126.1, 125.7,
125.5, 26.8.
We thank DST, India for financial support and D.S. is thankful to
CSIR, India for a Senior Research Fellowship. Crystallographic
studies were performed at the facility of the Department of In-
organic Chemistry, IACS; the authors thank Mr. Partha Haldar for
his valuable assistance.
d
d
4.1.22. 3-Phenylpyridine (4i).5a 1H NMR (300 MHz, CDCl3, ppm)
Supplementary data
d
8.85 (s, 1H), 8.59 (d, J¼3.2 Hz, 1H), 7.87 (d, J¼7.6 Hz, 1H), 7.57 (d,
J¼6.9 Hz, 2H), 7.50e7.35 (m, 4H); 13C NMR (75 MHz, CDCl3, ppm)
Supplementary data (contains copies of 1H and 13C and 31P NMR
spectra of all products listed in the tables) associated with this ar-
ticle provided as a separate file. Crystallographic data (excluding
structure factors) for the structures in this paper have been de-
posited with the Cambridge Crystallographic Data Centre as Sup-
plementary publication nos CCDC No. 890817 for L1 and CCDC No.
890818 for 1f. Copies of data can be obtained, free of charge, on
application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK
Supplementary data associated with this article can be found in
online version.
d
148.5, 148.3, 137.9, 136.8, 134.5, 129.2, 128.2, 127.2, 123.7.
4.1.23. 3-Cyano-2-phenylpyridine (4j).5a 1H NMR (300 MHz, CDCl3,
ppm) 8.86e8.84 (m, 1H), 8.07e8.04 (m, 1H), 7.94e7.91 (m, 2H),
7.53e7.51 (m, 3H), 7.37e7.34 (m, 1H); 13C NMR (75 MHz, CDCl3)
161.0, 152.7, 141.9, 137.2, 130.3, 128.9, 128.7, 121.6, 117.7, 107.5.
d
d
4.1.24. 2-Phenylpyridine (4k).5a 1H NMR (300 MHz, CDCl3, ppm)
8.73 (d, J¼4.8 Hz, 1H), 8.02 (d, J¼6.9 Hz, 2H), 7.78e7.76 (m, 2H),
7.53e7.44 (m, 3H), 7.26e7.19 (m, 1H); 13C NMR (75 MHz, CDCl3,
ppm) 157.5, 149.6, 139.3, 137.0, 129.5, 128.8, 127.1, 122.2, 120.8.
d
d
Supplementary data related to this article can be found at http://
4.1.25. 1-Benzyl-4-methoxybenzene (4l).5a 1H NMR (300 MHz,
CDCl3, ppm)
d 7.23e7.18 (m, 2H), 7.13e7.09 (m, 3H), 7.03 (d,
References and notes
J¼8.7 Hz, 2H), 6.76 (d, J¼8.6 Hz, 2H), 3.86 (s, 2H), 3.71 (s, 3H); 13C
1. For reviews, see: (a) Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44,
366; (b) Molander, G. A.; Canturk, B. Angew. Chem., Int. Ed. 2009, 48, 9240; (c)
Xue, L.; Lin, Z. Chem. Soc. Rev. 2010, 39, 1692.
NMR (75 MHz, CDCl3, ppm)
126.1, 114.0, 55.3, 41.2.
d 158.1, 141.7, 133.4, 130.0, 129.0, 128.6,
2. Selected reviews: (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176;
(b) Zapf, A.; Beller, M. Chem. Commun. 2005, 431; (c) Martin, R.; Buchwald, S. L.
Acc. Chem. Res. 2008, 41, 1461; (d) Hartwig, J. F. Nature 2008, 455, 314; (e) Fu, G.
C. Acc. Chem. Res. 2008, 41, 1555; (f) Enthaler, S.; Company, A. Chem. Soc. Rev.
2011, 40, 4912; (g) Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40,
4937; (h) So, C. M.; Kwong, F. Y. Chem. Soc. Rev. 2011, 40, 4963; (i) Wu, X. F.;
4.1.26. 1-[4-(Trifluoromethyl)benzyl]-4-methoxybenzene (4m).11 1H
NMR (300 MHz, CDCl3)
7.43 (d, J¼8.1 Hz, 2H), 7.18 (d, J¼8.0 Hz,
2H), 7.00 (d, J¼8.6 Hz, 2H), 6.76 (d, J¼8.6 Hz, 2H), 3.88 (s, 2H), 3.69
(s, 3H); 13C NMR (75 MHz, CDCl3)
158.4, 145.9, 132.2, 130.0, 129.2,
d
d