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Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones.
Org Biomol Chem. 2012 Sep 28; 10(36):7305-12.OB

Abstract

The remarkable catalytic effects of Fe(OTf)(3) in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO(2) to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kim D
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Korea.
Ham K
No affiliation info available
Hong S
No affiliation info available

MeSH

Boronic AcidsCatalysisChromonesFlavanonesFlavonesMolecular StructureOrganometallic CompoundsPalladium

Pub Type(s)

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

Language

eng

PubMed ID

22850763

Citation

Kim, Donghee, et al. "Synthetic Approach to Flavanones and Flavones Via Ligand-free palladium(II)-catalyzed Conjugate Addition of Arylboronic Acids to Chromones." Organic & Biomolecular Chemistry, vol. 10, no. 36, 2012, pp. 7305-12.
Kim D, Ham K, Hong S. Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones. Org Biomol Chem. 2012;10(36):7305-12.
Kim, D., Ham, K., & Hong, S. (2012). Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones. Organic & Biomolecular Chemistry, 10(36), 7305-12. https://doi.org/10.1039/c2ob26061a
Kim D, Ham K, Hong S. Synthetic Approach to Flavanones and Flavones Via Ligand-free palladium(II)-catalyzed Conjugate Addition of Arylboronic Acids to Chromones. Org Biomol Chem. 2012 Sep 28;10(36):7305-12. PubMed PMID: 22850763.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones. AU - Kim,Donghee, AU - Ham,Kyungrok, AU - Hong,Sungwoo, PY - 2012/8/2/entrez PY - 2012/8/2/pubmed PY - 2013/2/5/medline SP - 7305 EP - 12 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 36 N2 - The remarkable catalytic effects of Fe(OTf)(3) in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO(2) to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22850763/Synthetic_approach_to_flavanones_and_flavones_via_ligand_free_palladium_II__catalyzed_conjugate_addition_of_arylboronic_acids_to_chromones_ L2 - https://doi.org/10.1039/c2ob26061a DB - PRIME DP - Unbound Medicine ER -