Abstract
Activation of the CÍÄC bond in acetylenic hydrocarbons, catalyzed by iodide complexes of platinum(IV), and the subsequent CÄC coupling reaction make it possible to synthesize 1,4-diiodo-substituted dienes with high stereo- and regioselectivity. The reaction involves intermediate formation of bis-σ-vinyl platinum(IV) complexes which can be isolated in the pure state. Under similar conditions palladium(II) complexes catalyze iodine addition to acetylene.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Collman, J.P., Hegedus, L.S., Norton, J.R., and Finke, R.G., Principles and Application of Organo-transition Metal Chemistry, Mill Valley, California: University Science Books, 1987.
Yamamoto, A., Organotransition Metal Chemistry, New York: Wiley, 1986, pp. 54-70.
Temkin, O.N., Shestakov, G.K., and Treger, Yu.A., Atsetilen: Khimiya. Mekhanizmy reaktsii. Tekhnologiya (Acetylene: Chemistry. Reaction Mechanisms. Technology), Temkin, O.N., Ed., Moscow: Khimiya, 1991.
Crabtree, R.H., The Organometallic Chemistry of Transition Metals, New York: Wiley, 1988.
Tsuji, J., Palladium Reagents and Catalysis, Chichester: Wiley, 1995.
Mitchenko, S.A., Ananikov, V.P., Beletskaya, I.P., and Ustynyuk, Y.A., Mendeleev Commun., 1997, no. 4, pp. 130-131.
Ananikov, V., Mitchenko, S.A., Beletskaya, I.P., Nefedov, S.E., and Eremenko, I.L., Inorg. Chem. Commun., 1998, vol. 1, pp. 411-414.
Ananikov, V.P., Mitchenko, S.A., and Beletskaya, I.P., Dokl. Ross. Akad. Nauk, 1998, vol. 363, pp. 343-346.
Emsley, J.W., Feeney, J., and Sutcliffe, L.H., High-Resolution Nuclear Magnetic Resonance Spectroscopy, Oxford: Pergamon, 1966, vol. 2.
Hollins, R.A. and Campos, M.P.A., J. Org. Chem., 1979, vol. 44, pp. 3931-3934.
Transition Metal Nuclear Magnetic Resonance, Pregosin, P.S., Ed., Amsterdam: Elsevier, 1991, pp. 217-263.
Skvortsov, A.N., Russ. J. Gen. Chem., 2000, vol. 70, no. 7, pp. 1023-1027.
Stepin, B.D., Plyushchev, V.E., and Fakeev, A.A., Usp. Khim., 1965, vol. 34, pp. 1881-1907.
Wang, Z.Q., Humphies, P.S., and Maitlis, P.M., Book of Abstracts, XIth FECHEM Conf. on Organo-metallic Chemistry, Parma, Italy, 1995, p. 256.
CRC Handbook on Chemistry and Physics, Lide, D.R., Ed., CRC, 1996, 77th ed.
Sintez kompleksnykh soedinenii metallov platinovoi gruppy: Spravochnik (Synthesis of Coordination Compounds of the Platinum Group Metals. Handbook), Chernyaev, I.I., Ed., Moscow: Nauka, 1964.
Handbuch der Präparativen anorganischen Chemie, Bräuer, G., Ed., Stuttgart: Enke, 1981.
von Kienlin, M., Moonen, C.T.W., van der Toorn, A., and van Zijl, P.C.M., J. Magn. Reson., 1991, vol. 93, pp. 423-429.
Wagner, R. and Berger, S., J. Magn. Reson. A, 1996, vol. 123, pp. 229-232.
Bax, A. and Freeman, R., J. Magn. Reson., 1981, vol. 44, pp. 542-561.
Willker, W., Leibfritz, D., Kerrsebaum, R., and Bermel, W., Magn. Reson. Chem., 1993, vol. 31, pp. 287-292.
Ruiz-Cabello, J., Vuister, G.W., Moonen, C.T.W., van Gelderen, P., Cohen, J.S., and van Zijl, P.C.M., J. Magn. Reson., 1992, vol. 100, pp. 282-303.
Braun, S., Kalinowski, H.-O., and Berger, S., 150 and More Basic NMR Experiments, Weinheim: VCH, 1998.
Ionin, B.I., Ershov, B.A., and Kol'tsov, A.I., YaMR spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.
Bothner-By, A.A. and Jung, D., J. Am. Chem. Soc., 1968, vol. 90, pp. 2342-2346.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ananikov, V.P., Mitchenko, S.A. & Beletskaya, I.P. Stereo- and Regioselective Functionalization of Alkynes Catalyzed by Platinum(IV) and Palladium(II) Complexes in the System I--I3--H2O/MeOH. Russian Journal of Organic Chemistry 38, 636–650 (2002). https://doi.org/10.1023/A:1019646619165
Issue Date:
DOI: https://doi.org/10.1023/A:1019646619165