Abstract
The cross-coupling reactions of 4-bromo[2.2]paracyclophane withp-tolylmagnesium bromide in the presence of various palladium and nickel complexes have been studied. It was found that [1,1 ′-bis(diphenylphosphinoferrocene)]palladium dichloride (PdCl2 · dppf) shows the highest catalitic activity in this reaction. A series of new mono- and diaryl [2.2]paracyclophane derivatives with various substituents in the arene ring have been synthesized using this catalyst. It was shown that it is possible to cross-couple organozinc [2.2]paracyclophane derivatives with aromatic bromides. The composition and structure of the compounds obtained have been established on the basis of elemental analysis and spectral data. Some correlations between the structure and spectral parameters of mono- and diarylsubstituted [2.2]paracyclophanes have been found.
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References
D. J. Cram and D. L. Wilkinson,J. Am. Chem. Soc., 1960,82, 5721.
H. Ohno, H. Horita, T. Otsubo, Y. Sakata, and S. Misumi,Tetrahedron Lett., 1977, 265.
M. Stobbe, O. Reiser, T. Thiemann, R. J. Daniels, and A. de Meijere,Tetrahedron Lett., 1986,27, 2353.
V. I. Rozenberg, V. G. Kharitonov, E. V. Sergeeva, D. Yu. Antonov, and O. A. Reutov, inThesis Xth FECHEM Conference on Organometallic Chemistry, Agia Pelagia, Crete, Greece, 1993, 74.
S. C. Dickerman and N. Milstein,J. Org. Chem., 1967,32, 852.
L. Czuchajowski and A. Zemanek,Pol. J. Chem., 1990,64, 499.
P. Kuz and A. Zemanek,Pol. J. Chem., 1985,59, 281.
K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S.-i. Kodama, I. Nakajama, A. Minato, and M. Kumada,Bull. Chem. Soc. Jpn., 1976,49, 1958.
Cl. Feugeas,Bull. Soc. Chim. Fr., 1963,11, 2579.
J. L. Marshall and L. Hall,Tetrahedron, 1981,37, 1271.
N. A. Bumagin, I. G. Bumagina, and I. P. Beletskaya,Dokl. Akad. Nauk SSSR, 1984,274, 818 [Dokl. Chem., 1984,274 (Engl. Transl.)].
Ei.-i. Negishi, A. O. King, and N. Okukado,J. Org. Chem., 1977,42, 1821.
V. A. Nikanorov, V. I. Rozenberg, V. G. Kharitonov, E. V. Yatsenko, V. V. Mikul'shina, N. A. Bumagin, I. P. Beletskaya, V. N. Guryshev, V. P. Yur'ev, and O. A. Reutov,Metalloorg, Khim., 1991,4, 689 [Organomet. Chem. USSR, 1991,4 (Engl. Transl.)].
H. J. Reich and D. J. Cram,J. Am. Chem. Soc., 1969,91, 3534.
V. A. Nikanorov, V. G. Kharitonov, E. V. Yatsenko, D. P. Krut'ko, M. V. Galakhov, S. O. Yakushin, V. V. Mikul'shina, V. I. Rozenberg, V. N. Guryshev, V. P. Yur'ev, and O. A. Reutov,Izv. Akad. Nauk SSSR, Ser. Khim., 1992, 1837 [Bull. Russ. Akad. Nauk, Div. Chem. Sci., 1992,41, 1430 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1081–1085, June, 1994.
The present work was financially supported by the Russian Foundation for Basic Research (Project No. 93-03-5246).
The authors wish to express their gratitude to Prof. N. A. Bumagin for his scientific interest and helpful discussions.
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Rozenberg, V.I., Sergeeva, E.V., Kharitonov, V.G. et al. Synthesis of novel mono- and diaryl-substituted [2.2]paracyclophanes. Russ Chem Bull 43, 1018–1023 (1994). https://doi.org/10.1007/BF01558070
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DOI: https://doi.org/10.1007/BF01558070