Conclusions
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1.
Tin and sodium alkoxides, as well as tin amides, can be used as coreagents in the palladium complex-catalyzed carbonylation of aryl iodides. The use of such powerful nucleophiles as metal alkoxides and amides permits the carbonylation reactions to be carried out under milder conditions and at faster rates than those described in the literature.
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2.
A mechanism for the alkoxycarbonylation and amidation of aryl halides has been proposed based on results obtained using stoichiometric reactions of palladium complexes.
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Literature cited
H. Yoshida, N. Sugita, K. Kudo, and Y. Tagezaki, Nippon Kagaku Kaishi, 1386 (1974).
A. Schoenberg, I. Bartoletti, and R. F. Heck, J. Org. Chem.,39, 3318 (1974).
J. K. Stille and P. K. Wong, J. Org. Chem.,40, 352 (1975).
M. Hidai, T. Nikita, Y. Wada, Y. Fujikura, and Y. Uchida, Bull. Chem. Soc. Jpn.,48, 2075 (1975).
A. Cowell and J. K. Stille, J. Am. Chem. Soc.,102, 4193 (1980).
A. Schoenberg and R. F. Heck, J. Org. Chem.,39, 3327 (1974).
P. E. Garrou and R. F. Heck, J. Am. Chem. Soc.,98, 4115 (1976).
R. F. Heck, Platinum Met. Rev.,24, 58 (1980).
V. Gutman, Coordination Chemistry in Nonaqueous Solutions, Springer-Verlag (1968).
A. J. Gordan and R. A. Ford, A Chemist's Companion: A Handbook of Practical Data, Techniques and References, Wiley (1973).
J. K. Stille and K. S. Lau, Acc. Chem. Res.,10, 434 (1977).
G. W. Parshall, J. Am. Chem. Soc.,96, 2360 (1974).
T. Ito, K. Mori, T. Mizoroki, and A. Ozaki, Bull. Chem. Soc. Jpn.48, 2091 (1975).
J.-T. Chen and A. Sen, J. Am. Chem. Soc.,106, 1506 (1984).
F. Ozawa and A. Yamamoto, Chem. Lett., 865 (1982).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1649–1656, July, 1986.
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Bumagin, N.A., Gulevich, Y.V. & Beletskaya, I.P. Alkoxycarbonylation and amidation of aryl iodides catalyzed by palladium complexes. Russ Chem Bull 35, 1498–1504 (1986). https://doi.org/10.1007/BF00954834
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DOI: https://doi.org/10.1007/BF00954834