A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes

Konstantin Chernichenko, Ádám Madarász, I. Pápai, Martin Nieger, Markku Leskelä, Timo Repo

Research output: Contribution to journalArticle

195 Citations (Scopus)

Abstract

Frustrated Lewis pairs are compounds containing both Lewis acidic and Lewis basic moieties, where the formation of an adduct is prevented by steric hindrance. They are therefore highly reactive, and have been shown to be capable of heterolysis of molecular hydrogen, a property that has led to their use in hydrogenation reactions of polarized multiple bonds. Here, we describe a general approach to the hydrogenation of alkynes to cis-alkenes under mild conditions using the unique ansa-aminohydroborane as a catalyst. Our approach combines several reactions as the elementary steps of the catalytic cycle: hydroboration (substrate binding), heterolytic hydrogen splitting (typical frustrated-Lewis-pair reactivity) and facile intramolecular protodeborylation (product release). The mechanism is verified by experimental and computational studies.

Original languageEnglish
Pages (from-to)718-723
Number of pages6
JournalNature Chemistry
Volume5
Issue number8
DOIs
Publication statusPublished - Aug 2013

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Hydrogenation
Alkynes
Alkenes
Olefins
Hydrogen
Catalysts
Substrates

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Medicine(all)

Cite this

Chernichenko, K., Madarász, Á., Pápai, I., Nieger, M., Leskelä, M., & Repo, T. (2013). A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes. Nature Chemistry, 5(8), 718-723. https://doi.org/10.1038/nchem.1693

A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes. / Chernichenko, Konstantin; Madarász, Ádám; Pápai, I.; Nieger, Martin; Leskelä, Markku; Repo, Timo.

In: Nature Chemistry, Vol. 5, No. 8, 08.2013, p. 718-723.

Research output: Contribution to journalArticle

Chernichenko, K, Madarász, Á, Pápai, I, Nieger, M, Leskelä, M & Repo, T 2013, 'A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes', Nature Chemistry, vol. 5, no. 8, pp. 718-723. https://doi.org/10.1038/nchem.1693
Chernichenko, Konstantin ; Madarász, Ádám ; Pápai, I. ; Nieger, Martin ; Leskelä, Markku ; Repo, Timo. / A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes. In: Nature Chemistry. 2013 ; Vol. 5, No. 8. pp. 718-723.
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