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Organic carbonates as alternative solvents for palladium-catalyzed substitution reactions.
ChemSusChem. 2008; 1(3):249-53.C

Abstract

Organic carbonates, such as propylene carbonate, butylene carbonate, and diethyl carbonate, were tested in the Pd-catalyzed asymmetric allylic substitution reactions of rac-1,3-diphenyl-3-acetoxy-prop-1-ene with dimethyl malonate or benzylamine as nucleophiles. Bidentate diphosphanes were used as chiral ligands. The application of monodentate phosphanes capable of self-assembling with the metal was likewise tested. In the substitution reaction with dimethyl malonate, enantioselectivities up to 98% were achieved. In the amination reaction, the chiral product was obtained with up to 83% ee. The results confirm that these "green solvents" can be advantageously used for this catalytic transformation as an alternative to those solvents usually employed which run some risk of being harmful to the environment.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Schäffner B
Leibniz Institut für Katalyse e.V., Universität Rostock, Rostock, Germany.
Holz J
No affiliation info available
Verevkin SP
No affiliation info available
Börner A
No affiliation info available

MeSH

AlcoholsAllyl CompoundsAminationCarbonic AcidCatalysisHydrogenationLigandsOrganic ChemicalsPalladiumPhosphorusRhodiumSolvents

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18605214

Citation

Schäffner, Benjamin, et al. "Organic Carbonates as Alternative Solvents for Palladium-catalyzed Substitution Reactions." ChemSusChem, vol. 1, no. 3, 2008, pp. 249-53.
Schäffner B, Holz J, Verevkin SP, et al. Organic carbonates as alternative solvents for palladium-catalyzed substitution reactions. ChemSusChem. 2008;1(3):249-53.
Schäffner, B., Holz, J., Verevkin, S. P., & Börner, A. (2008). Organic carbonates as alternative solvents for palladium-catalyzed substitution reactions. ChemSusChem, 1(3), 249-53. https://doi.org/10.1002/cssc.200700142
Schäffner B, et al. Organic Carbonates as Alternative Solvents for Palladium-catalyzed Substitution Reactions. ChemSusChem. 2008;1(3):249-53. PubMed PMID: 18605214.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organic carbonates as alternative solvents for palladium-catalyzed substitution reactions. AU - Schäffner,Benjamin, AU - Holz,Jens, AU - Verevkin,Sergey P, AU - Börner,Armin, PY - 2008/7/9/pubmed PY - 2008/8/8/medline PY - 2008/7/9/entrez SP - 249 EP - 53 JF - ChemSusChem JO - ChemSusChem VL - 1 IS - 3 N2 - Organic carbonates, such as propylene carbonate, butylene carbonate, and diethyl carbonate, were tested in the Pd-catalyzed asymmetric allylic substitution reactions of rac-1,3-diphenyl-3-acetoxy-prop-1-ene with dimethyl malonate or benzylamine as nucleophiles. Bidentate diphosphanes were used as chiral ligands. The application of monodentate phosphanes capable of self-assembling with the metal was likewise tested. In the substitution reaction with dimethyl malonate, enantioselectivities up to 98% were achieved. In the amination reaction, the chiral product was obtained with up to 83% ee. The results confirm that these "green solvents" can be advantageously used for this catalytic transformation as an alternative to those solvents usually employed which run some risk of being harmful to the environment. SN - 1864-5631 UR - https://www.unboundmedicine.com/medline/citation/18605214/Organic_carbonates_as_alternative_solvents_for_palladium_catalyzed_substitution_reactions_ L2 - https://doi.org/10.1002/cssc.200700142 DB - PRIME DP - Unbound Medicine ER -