Abstract
Under the catalytic action of palladium,o-hydroxy- oro-amino-substituted aryl iodides oxidatively add to palladium(0), insert strained or rigid olefins, and close the ring between the aliphatic carbon and theortho-functional group. This reaction occurs under mild conditions in the absence of phosphine ligands in a DMF solution and affords fused dihydrofurans or-pyrroles.
Similar content being viewed by others
References
R. P. Hughes and J. Powell,J. Organomet. Chem., 1971,30, C45; M. C. Gallazzi, T. L. Hanlon, G. Vitulli, and L. Porri,J. Organomet. Chem., 1971,33, C45; R.C. Larock, S. S. Hershberger, K. Takagi, and M. A. Mitchell,J. Org. Chem., 1986,51, 2450; H. Horino, M. Arai, and N. Inoue,Tetrahedron Lett., 1974, 647; C. -S. Li, D. -C. Jou, and C. -H. Cheng,J. Chem. Soc., Chem. Commun., 1991, 710.
J. Sicher,Angew. Chem. Int. Ed. Eng., 1972,11, 200.
M. Catellani, G. P. Chiusoli, W. Giroldini, and G. SalernoJ. Organomet. Chem., 1980,199, C21.
M. Catellani and L. Ferioli,Synthesis, 1996, 769.
M. Catellani, G. P. Chiusoli, and C. Peloso,Tetrahedron Lett., 1983,24, 813; D. Roberto, M. Catellani, and G. P. Chiusoli,Tetrahedron Lett., 1988,29, 2115; R. van Asselt, E. E. C. G. Gielens, R. E. Rülke, and C. J. Elsevier,J. Chem. Soc., Chem. Commun., 1993, 1203; B. A. Markies, K. A. N. Verkerk, M. H. P. Rietveld, J. Boersma, H. Kooijman, A. L. Spek, and G. van Koten,J. Chem. Soc., Chem. Commun., 1993, 1317; M. Catellani,Izv. Akad. Nauk, Ser. Khim., 1995, 412 [Russ. Chem. Bull., 1995,44, 397 (Engl. Transl.)]; E. Dalcanale, Z. An, L. P. Battaglia, M. Catellani, and G. P. Chiusoli,J. Organomet. Chem., 1992,437, 375.
Z. An, M. Catellani, and G. P. Chiusoli,J. Organomet. Chem., 1989,371, C51; R. Grigg, K. Hashim, L. Philip, V. Julia, and S. Visuvanathar,Tetrahedron Lett., 1994,35, 3197.
Z. An, M. Catellani, and G. P. Chiusoli,Gazz. Chim. Ital., 1990,120, 383.
T. Jeffery,Adv. Met. Org. Chem., 1996,5, 153; T. Jeffery,Tetrahedron Lett., 1985,26, 2667.
Jpn. Pat. 07-53, 680, 1995;Chem Abstrs., 1995,123, P170669.
D. M. P. Mingos, inComprehensive Organometallic Chemistry, Eds. G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon Press, Oxford, 1982,3, 19.
R. E. Rinehart,J. Pol. Sci., Part C, 1966,27, 7.
H. E. Bryndza and W. Taw,Chem. Rev., 1988,88, 1163.
Author information
Authors and Affiliations
Additional information
Dipartimento di Chimica Organica e Industriale dell'Universita, Viale delle Scienze, I-43100 Parma, Italia.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 957–960, May, 1998.
Rights and permissions
About this article
Cite this article
Catellani, M., Del Rio, A. Catalytic arylation of carbon-carbon double bond followed by N- or O-cyclization. Russ Chem Bull 47, 928–931 (1998). https://doi.org/10.1007/BF02498163
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02498163