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Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones.
J Org Chem. 2021 09 03; 86(17):12318-12325.JO

Abstract

A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tamizharasan N
Supramolecular and Catalysis Lab, Department of Natural Products Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625021, Tamil Nadu, India. Medicinal Chemistry Department, Jubilant Biosys Ltd., Bangalore - 560022, Karnataka, India.
Hallur G
Medicinal Chemistry Department, Jubilant Biosys Ltd., Bangalore - 560022, Karnataka, India.
Suresh P
Supramolecular and Catalysis Lab, Department of Natural Products Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625021, Tamil Nadu, India.

MeSH

CatalysisIndenesIodidesMolecular StructurePalladium

Pub Type(s)

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

Language

eng

PubMed ID

34406781

Citation

Tamizharasan, Natarajan, et al. "Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones." The Journal of Organic Chemistry, vol. 86, no. 17, 2021, pp. 12318-12325.
Tamizharasan N, Hallur G, Suresh P. Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones. J Org Chem. 2021;86(17):12318-12325.
Tamizharasan, N., Hallur, G., & Suresh, P. (2021). Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones. The Journal of Organic Chemistry, 86(17), 12318-12325. https://doi.org/10.1021/acs.joc.1c01149
Tamizharasan N, Hallur G, Suresh P. Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones. J Org Chem. 2021 09 3;86(17):12318-12325. PubMed PMID: 34406781.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones. AU - Tamizharasan,Natarajan, AU - Hallur,Gurulingappa, AU - Suresh,Palaniswamy, Y1 - 2021/08/18/ PY - 2021/8/19/pubmed PY - 2021/8/19/medline PY - 2021/8/18/entrez SP - 12318 EP - 12325 JF - The Journal of organic chemistry JO - J Org Chem VL - 86 IS - 17 N2 - A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/34406781/Palladium_Catalyzed_Direct_α_Arylation_of_Indane_13_dione_to_2_Substituted_Indene_13_diones_ DB - PRIME DP - Unbound Medicine ER -