974
Russ.Chem.Bull., Int.Ed., Vol. 54, No. 4, April, 2005
Burukin et al.
(
C(2´)H); 133.19 (C(4)Cl); 134.43 (C(2)Cl). Mass spectrum,
S. Caddick, F. G. N. Clocke, A. P. Herring, and P. B.
Hitchcock, Tetrahedron Lett., 2004, 45, 3511; (h) I. J. S.
Fairlamb, A. R. Kapdi, and A. F. Lee, Org. Lett., 2004,
6, 4435.
+
m/z: 348 [M] .
The authors thank A. Z. Voskoboinikov, A. Yu.
Lebedev, A. N. Kasatkin, and D. S. Chekmarev for help
in the work.
3. (a) A. F. Indolese, Tetrahedron Lett., 1997, 38, 3513;
(b) M. B. Thathagar, J. Beckers, and G. Rothenberg, J. Am.
Chem. Soc., 2002, 124, 11858.
This work was financially supported by the Russian
Academy of Sciences (Fundamental Research Program
No. 1, Division of Chemistry and Materials Sciences,
Russian Academy of Sciences) and the Russian Science
Support Foundation.
4
. (a) M. Kumada, K. Tamao, and K. Sumitani, Org. Syntheꢀ
ses, 1978, 58, 127; (b) G. S. Reddy and W. Tam, Organoꢀ
metallics, 1984, 3, 630; (c) T. Katayama and M. Umeno,
Chem. Lett., 1991, 2073.
5
. M. Sonoda, A. Inaba, K. Itahashi, and Y. Tobe, Org. Lett.,
2
001, 3, 2419.
6. (a) N. Miyaura, T. Yanagi, and A. Suzuki, Synth. Commun.,
981, 11, 513; (b) S. Gronowitz, V. Bobosik, and K. Lawitz,
References
1
Chem. Scr., 1984, 23, 120; (c) B. I. Alo, A. Kandil, P. A.
Patil, M. J. Sharp, M. A. Siddiqui, and V. Snieckus, J. Org.
Chem., 1991, 56, 3763.
1
. (a) D. W. Old, J. P. Wolfe, and S. L. Buchwald, J. Am. Chem.
Soc., 1998, 120, 9722; (b) J. P. Wolfe, R. A. Singer, B. H.
Yang, and S. L. Buchwald, J. Am. Chem. Soc., 1999, 121,
7
8
. M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett.,
9
550; (c) A. F. Littke, C. Dai, and G. C. Fu, J. Am. Chem.
1
993, 34, 6403.
Soc., 2000, 122, 4020; (d) A. Zapf, R. Jackstell, F. Rataboul,
T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh,
U. Dingerdissen, and M. Beller, Chem. Commun., 2004, 38;
. (a) E. Negishi and F. Liu, in MetalꢀCatalyzed CrossꢀCoupling
Reactions, Eds F. Diederich and P. Stang, Weinheim,
WileyꢀVCH, 1998, p. 1; (b) P. Knochel, in MetalꢀCatalyzed
CrossꢀCoupling Reactions, Eds F. Diederich and P. Stang,
Weinheim, WileyꢀVCH, 1998, p. 387.
(
e) S. D. Walker, T. E. Barder, J. R. Martinelli, and S. L.
Buchwald, Angew. Chem., 2004, 116, 1907; (f) R. B. Bedford,
C. P. Butts, T. E. Hurst, and P. Lidström, Adv. Synth. Caꢀ
talysis, 2004, 346, 1627; (g) F. E. Kwong, K. S. Chan, C. H.
Yeung, and A. S. C. Chan, Chem. Commun., 2004, 2336;
9
. A. K. Gupta, C. Y. Rim, and C. H. Oh, Synlett, 2004, 2227.
1
1
0. A. J. Arduengo, R. Krafczyk, R. Schmutzler, H. A. Craig,
J. R. Goerlich, W. J. Marshall, and M. Unverzagt, Tetraꢀ
hedron, 1999, 55, 14523.
1. A. S. Burukin, A. A. Vasil´ev, M. I. Struchkova, V. V.
Kachala, and S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim.,
(
h) T. E. Barder and S. L. Buchwald, Org. Lett., 2004, 6,
2
3
2
649; (i) T. J. Colacot and H. A. Shea, Org. Lett., 2004, 6,
731; (j) C. Baillie, L. Zhang, and J. Xiao, J. Org. Chem.,
004, 69, 7779; (k) A. Mukherjee and A. Sarkar, Tetraꢀ
2
005, 941 [Russ. Chem. Bull., Int. Ed., 2005, 52, 964].
hedron Lett., 2004, 45, 9525; (l) W.ꢀM. Dai and Y. Zhang,
Tetrahedron Lett., 2005, 46, 1377.
1
1
1
2. D. S. Chekmarev, A. E. Stepanov, and A. N. Kasatkin,
Tetrahedron Lett., 2005, 46, 1303.
3. Y. Ahmad, M. I. Qureshi, and I. Baig, Can. J. Chem., 1967,
2
. (a) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck,
M. Grosche, and W. A. Herrmann, Angew. Chem., Int. Ed.
Engl., 2002, 41, 1363; (b) M. S. Viciu, R. F. Germaneau,
O. NavarroꢀFernandez, E. D. Stevens, and S. P. Nolan,
Organometallics, 2002, 21, 5470; (c) G. Altenhoff,
R. Goddard, C. W. Lehmann, and F. Glorius, Angew. Chem.,
Int. Ed. Engl., 2003, 42, 3690; (d) O. Navarro, H. Kaur,
P. Mahjoor, and S. P. Nolan, J. Org. Chem., 2004, 69, 3173;
4
5, 1539.
4. (a) M. Yanagisawa, K. Hayamizu, and O. Yamamoto,
Magn. Res. Chem., 1986, 24, 1013; (b) M. Yanagisawa,
K. Hayamizu, and O. Yamamoto, Magn. Res. Chem., 1987,
2
5, 184.
1
5. (a) A. E. Jukes, S. S. Dua, and H. Gilman, J. Organomet.
Chem., 1970, 24, 791; (b) M. Wada, K. Kusabe, and
K. Oguro, Inorg. Chem., 1977, 16; 446.
(
e) O. Navarro, Y. Oonishi, R. A. Kelly, E. D. Stevens,
O. Briel, and S. P. Nolan, J. Organomet. Chem., 2004, 689,
722; (f) H. Lebel, M. K. Janes, A. B. Charette, and S. P.
Nolan, J. Am. Chem. Soc., 2004, 126, 5046; (g) K. Arentsen,
3
Received April 1, 2005