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The Cp2ZrCl2-catalyzed cycloalumination of functionally substituted olefins with triethylaluminum

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Abstract

Reactions of functionally substituted olefins (allylamines, sulfides and ethers, homoallylic alcohols and amines, as well as vinyl ethers) with Et3Al in the presence of Cp2ZrCl2 as a catalyst were studied. Cycloalumination of allylamines occurs with high regioselectivity to furnish after subsequent deuterolysis 4-deutero-2-(deuteromethyl)butyl-substituted amines. Cycloalumination of alkyl allyl sulfide is accompanied by a side process of the C-S bond cleavage. In the case of allyl and vinyl ethers, no cycloalumination products are formed under the reaction conditions. However, the reactions with homoallylic alcohol and amine after deuterolysis gave the corresponding dideutero-containing compounds in good yields.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    I. R. Ramazanov, R. N. Kadikova & U. M. Dzhemilev

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  1. I. R. Ramazanov
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  2. R. N. Kadikova
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  3. U. M. Dzhemilev
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Correspondence to I. R. Ramazanov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1602–1606, August, 2011.

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Ramazanov, I.R., Kadikova, R.N. & Dzhemilev, U.M. The Cp2ZrCl2-catalyzed cycloalumination of functionally substituted olefins with triethylaluminum. Russ Chem Bull 60, 1628–1632 (2011). https://doi.org/10.1007/s11172-011-0243-3

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  • DOI: https://doi.org/10.1007/s11172-011-0243-3

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