7
60
H. Chaumeil et al.
PAPER
References
D.; Walker, J.; Wojcik, R.; Zorn, C. Trans. Nucl. Sci. 1989,
3
6, 562. (c) See also: De Vol, T. A.; Wehe, D. K.; Knoll, G.
K. Nucl. Instrum. Methods Phys. Res., Sect. A 1994, 348,
56. (d) See also: Ikoma, Y.; Taya, F.; Naoi, Y. Japanese
Patent 0183030, 1989; Chem. Abstr. 1989, 111, 153333. (e)
,4-Bis(4-methoxyphenyl)benzene: Yamada, S.; Tanabe, S.
Japanese Patent 07101900, 1995; Chem. Abstr. 1995, 123,
70537. (f) Linear optical materials, 1,4-bis(4-
(
(
1) Chaumeil H., Le Drian C. 31ème séminaire Hors-Ville
d’Automne and 21st Regio Symposium in Organic and
Bioorganic chemistry, 16–20th September 2001, Champery,
Switzerland.
2) (a) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749. (b) Heck,
R. F. Palladium Reagents in Organic Syntheses; Academic
Press: London, 1985. (c) Matteson, D. S. Tetrahedron 1989,
1
1
1
methoxyphenyl)benzene: Kauffman, J. M.; Kelley, C. S.;
Ghiorghis, A.; Neister, E.; Seliskar, C. J.; Steppel, R. N.
Proc. Int. Conf. Lasers 1989, 420. (g) 1,4-Bis(2-
methylphenyl)benzene: Golovkin, S. V.; Konstantinchenko,
A. A.; Koslov, V. A.; Kushnirenko, A. E.; Pyschchev, A. I.;
Shershukov, V. M.; Vasil’chenko, V. G.; Zimyn, K. V. Nucl.
Instrum. Methods Phys. Res,. Sect. A 1995, 362, 283.
45, 1859. (d) Martin, A. R.; Yang, Y. Acta Chem. Scand.
1993, 47, 221. (e) Suzuki, A. Pure Appl. Chem. 1994, 66,
213. (f) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(
g) Tsuji, J. Palladium Reagents and Catalysts; Wiley:
Chichester, 1995. (h) Stanforth, S. P. Tetrahedron 1998, 54,
63. (i) Suzuki, A. J. Organomet. Chem. 1999, 147.
2
(
3) (a) Schlüter, A. D. J. Polym. Sci., Polym. Chem. 2001, 1533;
and references cited therein. (b) Synthesis of biaryls
possessing three or four ortho-substituents by cross-
coupling in the presence of Pd(PPh ) : Miller, R. B.; Dugar,
(
h) See also: Kessler, W. J.; Davis, S. J.; Ferguson, D. R.;
Pugh, E. R. US Patent 5610932, 1997; Chem. Abstr. 1997,
26, 256922.
(9) (a) Banfi, S.; Montanari, F.; Pozzi, G.; Quici, S. Tetrahedron
994, 50, 9025. (b) Houk, K. N.; Menzer, S.; Newton, S. P.;
1
3
4
S. Organometallics 1984, 3, 1261. (c) See also: Muller, D.;
Fleury, J.-P. Tetrahedron Lett. 1991, 32, 2229. (d) See also:
Fu, J.-M.; Zhao, B.-P.; Sharp, M. J.; Sniekus, V. J. Org.
Chem. 1991, 56, 1653. (e) See also: Watanabe, T.; Miyaura,
N.; Suzuki, A. Synlett 1992, 207. (f) See also: Zhang, H.;
Xue, F.; Mak, T. C. W.; Chan, K.-S. J. Org. Chem. 1996, 61,
1
Raymo, F. M.; Stoddart, J. F.; Williams, D. J. J. Am. Chem.
Soc. 1999, 121, 1479.
(
10) (a) Todd, M. H.; Balasubramanian, S.; Abell, C.
Tetrahedron Lett. 1997, 38, 6781. (b) Schilling, B.;
Kaufmann, D. E. Eur. J. Org. Chem. 1998, 701.
8002. (g) See also: Zhang, H.; Chan, K.-S. Tetrahedron Lett.
(
(
c) Newnan, M. S.; Hung, W. J. Org. Chem. 1974, 39, 3950.
d) Hart, H.; Harada, K.; Frank Du, C.-J. J. Org. Chem.
1996, 37, 1043. (h) See also: Anderson, J. C.; Namli, H.;
Roberts, C. A. Tetrahedron 1997, 53, 15123. (i) See also:
Jonhson, M. G.; Foglesong, R. J. Tetrahedron Lett. 1997, 38,
1
985, 50, 3104. (e) Ikoma, Y.; Taya, F.; Ozaki, E.-I.;
Higuchi, S.; Naoi, Y.; Fuji-i, K. Synthesis 1990, 147.
f) Ikoma, Y.; Ando, K.; Naoi, Y.; Akiyama, T.; Sugimori,
7001. (j) See also: Zhang, H.; Kwong, F.-Y.; Tian, Y.; Chan,
(
K.-S. J. Org. Chem. 1998, 63, 6886. (k) See also:
Kamikawa, T.; Hayashi, T. Tetrahedron 1999, 55, 3455.
4) (a) Thomson, W. J.; Gaudino, J. J. Org. Chem. 1984, 49,
A. Synth. Commun. 1991, 481.
(
(
11) Shoesmith, J. B.; Mackie, A. J. Am. Chem. Soc. 1928, 2338.
12) Wirth, H. O.; Königstein, O.; Kern, W. Liebigs Ann. Chem.
(
5237. (b) Gronowitz, S.; Bobosik, V.; Lawitz, K. Chem. Scr.
1960, 634, 84.
1984, 23, 120. (c) Gronowitz, S.; Honfelt, A.-B.; Yang, Y.
(
(
13) Mc Closkey, C. M.; Coleman, G. H. Org. Synth. Coll. Vol. 3;
Wiley: New York, 1955, 434.
14) Kornblum, N.; Lurie, A. P. J. Am. Chem. Soc. 1959, 81,
Chem. Scr. 1988, 28, 281. (d) Abraham, M. H.; Grellier, P.
L. The Chemistry of the Metal Carbon Bond; Hartley, F. R.;
Patai, S., Eds.; Wiley: New York, 1985.
2710.
(
(
(
(
5) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett.
(
(
15) Cotton, F. A. Inorg. Synth. 1972, 13, 121.
16) Uemura, S.; Tanaka, S.; Okamo, R. M.; Hamana, M. J. Org.
Chem. 1983, 48, 3297.
17) (a) Coutts, I. G. C.; Goldschmid, H. R.; Musgrave, O. C. J.
Chem. Soc. C 1970, 488. (b) Miller, W. T.; Koch, S. D. J.
Am. Chem. Soc. 1957, 79, 3081.
18) Wasgindt, M.; Klemm, E. Synth. Commun. 1999, 29, 103.
19) Colonge, J.; Buendia, J.; Sabadie, J. Bull. Soc. Chim. Fr.
2
001, 42, 6667; and references cited therein.
6) Hoshino, Y.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn.
988, 61, 3008.
7) Chaumeil, H.; Signorella, S.; Le Drian, C. Tetrahedron
000, 56, 9655.
1
(
2
8) (a) 1,4-bis(4-methoxyphenyl)benzene: Danjo, S.; Saito, T.;
Kadomachi, H.; Kishimoto, D. Japanese Patent 03250021,
(
(
1991; Chem. Abstr. 1992, 116, 129935. (b) 1,4-bis(2-
1
967, 4370.
20) Prince, C. C.; Mueller, G. P. J. Am. Chem. Soc. 1944, 66,
32.
21) (a) Böckmann, K.; Vögtle, F. Liebigs Ann. Chem. 1981,
67. (b) Wirth, H. O.; Gönner, K. H.; Stück, R.; Kern, W.
methylphenyl)benzene: Dowen, M.; Majewski, S.; Pettey,
(
(
6
4
Makromol. Chem. 1963, 63, 30.
(
22) Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 3126.
Synthesis 2002, No. 6, 757–760 ISSN 0039-7881 © Thieme Stuttgart · New York