4
080
W.-T. Shu et al.
FEATURE ARTICLE
Mihovilovic, M. D. J. Org. Chem. 2005, 70, 5215.
(c) Hadei, N.; Kantchev, E. A. B.; O’Brien, C. J.; Organ, M.
G. J. Org. Chem. 2005, 70, 8503. (d) Huang, Z.; Qian, M.;
Babinski, D. J.; Negishi, E.-I. Organometallics 2005, 24,
4
-Methoxy-4¢-methylbiphenyl (2p)5b
Yield: 0.161 g (81%); white solid.
1
H NMR (400 MHz, CDCl ): d = 7.52–7.50 (m, 2 H), 7.46–7.44 (m,
3
2
3
H), 7.24–7.22 (m, 2 H), 6.98–6.96 (m, 2 H), 3.85 (s, 3 H), 2.38 (s,
H).
475. (e) Xu, H.; Ekoue-Kovi, K.; Wolf, C. J. Org. Chem.
2
008, 73, 7638. (f) Sase, S.; Jaric, M.; Metzger, A.;
1
3
1
C{ H} NMR (100 MHz, CDCl ): d = 158.9, 137.9, 136.3, 133.7,
3
Malakhov, V.; Knochel, P. J. Org. Chem. 2008, 73, 7380.
g) Manolikakes, G.; Dong, Z. B.; Mayr, H.; Li, J. S.;
1
29.4, 127.9, 126.5, 114.1, 55.3, 21.0.
(
Knochel, P. Chem. Eur. J. 2009, 15, 1324.
7) (a) Martin, R.; Fürstner, A. Angew. Chem. Int. Ed. 2004, 43,
4
-Methoxy-4¢-trimethylsilylbiphenyl (2q)30
(
Yield: 0.195 g (76%); yellow solid.
3955. (b) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
1
(c) Yoshikai, N.; Mashima, H.; Nakamura, E. J. Am. Chem.
Soc. 2005, 127, 17978. (d) Bedford, R. B.; Betham, M.;
Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M.
J. Org. Chem. 2006, 71, 1104. (e) Leleu, A.; Fort, Y.;
Schneider, R. Adv. Synth. Catal. 2006, 348, 1086. (f) Wolf,
C.; Xu, H. H. J. Org. Chem. 2008, 73, 162.
H NMR (400 MHz, CDCl ): d = 7.61–7.54 (m, 6 H), 7.00–6.98 (m,
3
2
H), 3.84 (s, 3 H), 0.32 (s, 9 H).
1
3
1
C{ H} NMR (100 MHz, CDCl ): d = 159.2, 141.2, 138.4, 133.8,
3
1
33.6, 128.1, 126.0, 114.2, 55.2, –1.1.
4
-Methoxy-2-naphthylbenzene (2r)9d
(
2
g) Manolikakes, G.; Knochel, P. Angew. Chem. Int. Ed.
009, 48, 205. (h) Hartmann, C. E.; Nolan, S. P.; Cazin, C.
S. J. Organometallics 2009, 28, 2915.
Yield: 0.211 g (90%); white solid.
1
H NMR (400 MHz, CDCl ): d = 7.99 (s, 1 H), 7.91–7.85 (m, 3 H),
3
7
.73–7.65 (m, 3 H), 7.51–7.44 (m, 2 H), 7.05–7.01 (m, 2 H), 3.88
(8) (a) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41,
4176. (b) Hu, Q.-S.; Lu, Y.; Tang, Z.-Y.; Yu, H.-B. J. Am.
Chem. Soc. 2003, 125, 2856. (c) Bedford, R. B.; Blake, M.
E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466.
(
s, 3 H).
1
3
1
C{ H} NMR (100 MHz, CDCl ): d = 159.2, 138.1, 133.7, 133.6,
3
1
5
32.3, 128.4, 128.3, 128.0, 127.6, 126.2, 125.6, 125.4, 125.0, 114.3,
(
d) Miura, M. Angew. Chem. Int. Ed. 2004, 43, 2201.
5.3.
(
e) Zhou, L.; Miao, Q.; He, R.; Feng, X.; Bao, M.
+
HRMS (EI): m/z calcd for C H O [M ]: 234.1045; found:
2
1
7
14
Tetrahedron Lett. 2007, 48, 7899. (f) Hoshi, T.; Nakazawa,
T.; Saitoh, I.; Mori, A.; Suzuki, T.; Sakai, J.; Hagiwara, H.
Org. Lett. 2008, 10, 2603. (g) So, C. M.; Yeung, C. C.; Lau,
C. P.; Kwong, F. Y. J. Org. Chem. 2008, 73, 7803.
34.1049.
Acknowledgment
(
9) (a) Munday, R. H.; Martinelli, J. R.; Buchwald, S. L. J. Am.
Chem. Soc. 2008, 130, 2754. (b) Quasdorf, K. W.; Tian, X.;
Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422.
Financial support under grant number NSC 96-2113-M-005-007-
MY3 from the National Science Council of Taiwan is appreciated.
(
c) Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem.
Int. Ed. 2008, 47, 4866. (d) Guan, B.-T.; Wang, Y.; Li, B.-
J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130,
References
1
4468. (e) Fors, B. P.; Watson, D. A.; Biscoe, M. R.;
Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552.
f) Li, B.-J.; Li, Y.-Z.; Lu, X.-Y.; Liu, J.; Guan, B.-T.; Shi,
Z.-J. Angew. Chem. Int. Ed. 2008, 47, 10124.
g) Ackermann, L.; Althammer, A.; Fenner, S. Angew.
Chem. Int. Ed. 2009, 48, 201.
10) (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars,
A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
(
1) (a) Bringmann, G.; Gunther, C.; Ochse, M.; Schupp, O.;
Tasler, S. Progress in the Chemistry of Organic Natural
Products, Vol. 82; Herz, W.; Falk, H.; Kirby, G. W.; Moore,
R. E., Eds.; Springer: New York, 2001, 1–293.
(
(
(
b) Noguchi, H.; Hojo, K.; Suginome, M. J. Am. Chem. Soc.
007, 129, 758.
2) (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire,
2
(
(
(
(
M. Chem. Rev. 2002, 102, 1359. (c) Miyaura, N. Top. Curr.
(c) Chen, Y.-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609.
Chem. 2002, 219, 11.
3) (a) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc.
(
d) Hill, L. L.; Moore, L. R.; Huang, R. C.; Craciun, R.;
(
Vincent, A. J.; Dixon, D. A.; Chou, J.; Woltermann, C. J.;
Shaughnessy, K. H. J. Org. Chem. 2006, 71, 5117.
2
003, 125, 16194. (b) Moore, L. R.; Shaughnessy, K. H.
Org. Lett. 2004, 6, 225. (c) Dong, C.-G.; Hu, Q.-S. J. Am.
Chem. Soc. 2005, 127, 10006. (d) Barder, T. E.; Walker, S.
D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc.
(
e) Biscoe, M. R.; Fors, B. P.; Buchwald, S. L. J. Am. Chem.
Soc. 2008, 130, 6686. (f) Fors, B. P.; Watson, D. A.; Biscoe,
M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552.
2
005, 127, 4685. (e) González-Bobes, F.; Fu, G. C. J. Am.
(
g) Zhu, L. B.; Li, G. C.; Luo, L.; Guo, P.; Lan, J. B.; You,
Chem. Soc. 2006, 128, 5360. (f) Imao, D.; Glasspoole, B.
W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009,
J. S. J. Org. Chem. 2009, 74, 2200.
(
11) (a) Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S.
L. J. Am. Chem. Soc. 2001, 123, 10770. (b) Kataoka, N.;
Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem.
1
31, 5024.
4) (a) Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed.
004, 43, 4704. (b) Su, W.; Urgaonkar, S.; McLaughlin, P.
A.; Verkade, J. G. J. Am. Chem. Soc. 2004, 126, 16433.
c) Powell, D. A.; Maki, T.; Fu, G. C. J. Am. Chem. Soc.
005, 127, 510. (d) Chiappe, C.; Pieraccini, D.; Zhao, D.;
(
2
2
002, 67, 5553. (c) Vorogushin, A. V.; Huang, X.;
Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146.
d) Gooßen, L. J.; Gooßen, K.; Stanciu, C. Angew. Chem.
(
2
(
Int. Ed. 2009, 48, 3569.
Fei, Z.; Dyson, P. J. Adv. Synth. Catal. 2006, 348, 68.
5) (a) Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137.
(
12) (a) Li, G. Y. Angew. Chem. Int. Ed. 2001, 40, 1513.
(
(b) Fernández-Rodríguez, M. A.; Shen, Q. L.; Hartwig, J. F.
(
b) Sahoo, A. K.; Oda, T.; Nakao, Y.; Hiyama, T. Adv. Synth.
Chem. Eur. J. 2006, 12, 7782. (c) Maitro, G.; Vogel, S.;
Sadaoui, M.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2007,
Catal. 2004, 346, 1715. (c) Shi, S. Y.; Zhang, Y. H. J. Org.
Chem. 2007, 72, 5927.
6) (a) Wiskur, S. L.; Korte, A.; Fu, G. C. J. Am. Chem. Soc.
9, 5493.
(
2004, 126, 82. (b) Stanetty, P.; Hattinger, G.; Schnürch, M.;
Synthesis 2009, No. x, 4075–4081 © Thieme Stuttgart · New York