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Recoverable polystyrene-supported palladium catalyst for construction of all-carbon quaternary stereocenters via asymmetric 1,4-addition of arylboronic acids to cyclic enones

The development of recoverable catalysts based on the combination of synthetically demanding ligands with transition metals attracts a lot of attention, especially from the environmental point of view. In this paper, we describe the preparation of a recoverable polystyrene supported chiral palladium...

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Published in:Reactive & functional polymers 2020-08, Vol.153, p.104615, Article 104615
Main Authors: Bartáček, Jan, Váňa, Jiří, Drabina, Pavel, Svoboda, Jan, Kocúrik, Martin, Sedlák, Miloš
Format: Article
Language:English
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Summary:The development of recoverable catalysts based on the combination of synthetically demanding ligands with transition metals attracts a lot of attention, especially from the environmental point of view. In this paper, we describe the preparation of a recoverable polystyrene supported chiral palladium catalyst based on PyOx ligand suitable for asymmetric 1,4-addition of arylboronic acids to cyclic 3-substituted five- and six-membered enones. In the reaction, all‑carbon quaternary stereocenters are formed with a high level of enantioselectivity (up to 91% ee) and conversion (up to 99%). The catalyst was used in 6 cycles with no loss of enantioselectivity and only a small decrease in conversion. A solution of the problems associated with the transition from homogeneous to heterogeneous catalytic systems is discussed. [Display omitted] •Recoverable polystyrene supported chiral palladium catalyst based on PyOx ligand was prepared.•The catalyst was used for asymmetric 1,4-addition of arylboronic acids to cyclic 3-substituted five- and six-membered enones.•All-carbon quaternary stereocenters are formed with a high level of enantioselectivity and conversion.•The catalyst was used in 6 cycles with no loss of enantioselectivity and only a small decrease in conversion.
ISSN:1381-5148
1873-166X
DOI:10.1016/j.reactfunctpolym.2020.104615