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The versatility of metal halide-quaternary ammonium salt catalysts for organic processes. From homogeneous to glass-encapsulated ion pairs

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Abstract

Ion pairs generated from transition metal halides and quaternary onium salts are versatile catalysts for many organic processes. Under phase transfer conditions, RhCl3- and/or PtCl4-Aliquat 336® catalyze (a) double bond migration in allylic compounds, (b) disproportionation of cyclic 1,3-dienes, (c) selective transfer reduction of alkenes, alkynes, α,β-carbonyl compounds, and aroyl chlorides by polymethylhydrosiloxane, (d) hydrogenation of double, triple, and aromatic C-C bonds at room temperature, (e) cyclooligomerization of mono-, di-, and triacetylenes, and (f) addition of water, sulfur, and carbon monoxide to alkynes. In processes (a)-(c) the metal catalyst can be recovered in the aqueous phase by treatment of the reaction mixture with lipophilic anions. Two alternative methods for the recovery of the ion pair catalysts have been investigated. One is based on catalyst encapsulation in sol-gel matrices and the other employs polystyrene-supported ion pairs.

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Authors and Affiliations

  1. Department of Organic Chemistry, The Hebrew University, 91904, Jerusalem, Israel

    Jochanan Blum

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  1. Jochanan Blum
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Translated fromIzvestiya Akademii Nauk. Serlya Khimicheskaya, No. 10, pp. 1697–1705, October, 1993.

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Blum, J. The versatility of metal halide-quaternary ammonium salt catalysts for organic processes. From homogeneous to glass-encapsulated ion pairs. Russ Chem Bull 42, 1619–1627 (1993). https://doi.org/10.1007/BF00697026

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