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G. A. Molander et al.
CLUSTER
7.68–7.64 (m, 4 H), 7.55 (d, J = 8.8 Hz, 2 H), 7.00 (d, J = 8.8 Hz, 2
H), 3.86 (s, 3 H). 13C NMR (125 MHz, CDCl3): d = 160.0, 144.4,
132.3, 128.8 (q, JCF = 32.6 Hz), 128.5, 127.0, 125.8 (q, JCF = 3.8
Hz), 125.6 (q, JCF = 271.6 Hz), 114.6, 55.5.
References
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1995, 95, 2457.
1-(4-Methoxyphenyl)naphthalene21
(2) Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2003, 4313.
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General procedure A was used, but the reaction was heated at reflux
for 3.5 h. Yield 71%. Product appearance: off-white solid; mp 113–
115 °C; Rf = 0.11 (1% EtOAc–hexanes). 1H NMR (500 MHz,
CDCl3): d = 8.00 (d, J = 7.9 Hz, 1 H), 7.95 (d, J = 8.4 Hz, 1 H), 7.90
(d, J = 8.4 Hz, 1 H), 7.59–7.45 (m, 6 H), 7.11–7.08 (m, 2 H), 3.94
(s, 3 H). 13C NMR (125 MHz, CDCl3): d = 159.1, 140.0, 134.0,
133.3, 132.0, 131.2, 128.4, 127.5, 127.0, 126.2, 126.0, 125.8, 125.5,
113.9, 55.4.
2-(4-Trifluoromethylphenyl)naphthalene
General procedure A was used, but the reaction was heated at reflux
for 24 h. Yield 92%. Product appearance: white solid; mp 127–129
°C; Rf = 0.35 (EtOAc–hexanes 1%). 1H NMR (500 MHz, CDCl3):
d = 8.08 (s, 1 H), 7.99–7.89 (m, 3 H), 7.85–7.77 (m, 5 H), 7.60–7.53
(m, 2 H). 13C NMR (125 MHz, CDCl3): d = 144.8, 137.2, 133.7,
133.1, 129.5 (q, JCF = 32.6 Hz), 128.9, 128.5, 127.8, 127.8, 126.7,
126.6, 126.5, 125.9 (q, JCF = 3.8 Hz), 125.3, 124.5 (q, JCF = 271.6
Hz). IR (KBr): 3062, 2368, 1926, 1617, 1595, 1503, 1436, 1408,
1339, 1114, 1076, 1009 cm–1. Anal. Calcd for C17H11F3: C, 74.99;
H, 4.07. Found: C, 75.04; H, 3.98.
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Acknowledgment
The authors wish to thank the NIH, Johnson & Johnson, Merck Re-
search Laboratories, and Amgen for their support of this program.
We thank Johnson-Matthey for the generous donation of palladium
catalysts used in this study.
(20) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058.
(21) Denmark, S. E.; Ober, M. H. Org. Lett. 2003, 5, 1357.
Synlett 2005, No. 11, 1763–1766 © Thieme Stuttgart · New York