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Catalytic olefination of carbonyl compounds. A new versatile method for the synthesis of alkenes

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Abstract

The review is devoted to a new catalytic olefination reaction (COR) discovered by the authors. This is the reaction between N-unsubstituted hydrazones of carbonyl compounds with dihalides CHal2XY in the presence of copper(i) chloride to give substituted alkenes. Catalytic olefination is versatile. Variation of the carbonyl and olefinating components opens up the way for the synthesis of various classes of unsaturated compounds including those containing functional groups. The reaction mechanism is discussed and a catalytic cycle describing the process is proposed. A model for estimating and predicting the reactivity of halogen-containing compounds in the COR is developed. The relationship between the structure of the carbonyl substrates and their behavior in the title reaction is elucidated.

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  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992, Moscow, Russian Federation

    V. G. Nenajdenko, V. N. Korotchenko & E. S. Balenkova

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation

    A. V. Shastin

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  1. V. G. Nenajdenko
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  3. A. V. Shastin
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  4. E. S. Balenkova
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Nenajdenko, V.G., Korotchenko, V.N., Shastin, A.V. et al. Catalytic olefination of carbonyl compounds. A new versatile method for the synthesis of alkenes. Russian Chemical Bulletin 53, 1034–1064 (2004). https://doi.org/10.1023/B:RUCB.0000041302.14763.72

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