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Copper-catalyzed direct synthesis of diaryl 1,2-diketones from aryl iodides and propiolic acids.
J Org Chem. 2014 Jul 03; 79(13):6279-85.JO

Abstract

Benzil derivatives such as diaryl 1,2-diketones are synthesized via the direct decarboxylative coupling reaction of aryl propiolic acids and their oxidation. The optimized conditions are that the reaction of aryl propiolic acids and aryl iodides is conducted at 140 °C for 6 h in the presence of 10 mol % CuI/Cu(OTf)2 and Cs2CO3, after which HI (aq) is added and further reacted. The method shows good functional group tolerance toward ester, aldehyde, cyano, and nitro groups. In addition, symmetrical diaryl 1,2-diketones are obtained from aryl iodides and propiolic acid in the presence of palladium and copper catalysts.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Min H
Department of Chemistry, Chonnam National University , Gwangju 500-757, Republic of Korea.
Palani T
No affiliation info available
Park K
No affiliation info available
Hwang J
No affiliation info available
Lee S
No affiliation info available

MeSH

AlkynesCatalysisCopperIodidesKetonesMolecular StructureOxidation-ReductionPalladiumPhenylglyoxalPropionates

Pub Type(s)

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

Language

eng

PubMed ID

24958126

Citation

Min, Hongkeun, et al. "Copper-catalyzed Direct Synthesis of Diaryl 1,2-diketones From Aryl Iodides and Propiolic Acids." The Journal of Organic Chemistry, vol. 79, no. 13, 2014, pp. 6279-85.
Min H, Palani T, Park K, et al. Copper-catalyzed direct synthesis of diaryl 1,2-diketones from aryl iodides and propiolic acids. J Org Chem. 2014;79(13):6279-85.
Min, H., Palani, T., Park, K., Hwang, J., & Lee, S. (2014). Copper-catalyzed direct synthesis of diaryl 1,2-diketones from aryl iodides and propiolic acids. The Journal of Organic Chemistry, 79(13), 6279-85. https://doi.org/10.1021/jo501089k
Min H, et al. Copper-catalyzed Direct Synthesis of Diaryl 1,2-diketones From Aryl Iodides and Propiolic Acids. J Org Chem. 2014 Jul 3;79(13):6279-85. PubMed PMID: 24958126.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed direct synthesis of diaryl 1,2-diketones from aryl iodides and propiolic acids. AU - Min,Hongkeun, AU - Palani,Thiruvengadam, AU - Park,Kyungho, AU - Hwang,Jinil, AU - Lee,Sunwoo, Y1 - 2014/06/24/ PY - 2014/6/25/entrez PY - 2014/6/25/pubmed PY - 2014/12/15/medline SP - 6279 EP - 85 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 13 N2 - Benzil derivatives such as diaryl 1,2-diketones are synthesized via the direct decarboxylative coupling reaction of aryl propiolic acids and their oxidation. The optimized conditions are that the reaction of aryl propiolic acids and aryl iodides is conducted at 140 °C for 6 h in the presence of 10 mol % CuI/Cu(OTf)2 and Cs2CO3, after which HI (aq) is added and further reacted. The method shows good functional group tolerance toward ester, aldehyde, cyano, and nitro groups. In addition, symmetrical diaryl 1,2-diketones are obtained from aryl iodides and propiolic acid in the presence of palladium and copper catalysts. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24958126/Copper_catalyzed_direct_synthesis_of_diaryl_12_diketones_from_aryl_iodides_and_propiolic_acids_ DB - PRIME DP - Unbound Medicine ER -