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Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones.
Chemistry. 2021 Dec 15; 27(70):17688-17694.C

Abstract

A ligand-controlled site-selective C(sp3)-H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- to β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C-H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion.

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Authors+Show Affiliations

Kudashev A
Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056, Basel, Switzerland.
Baudoin O
Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056, Basel, Switzerland.

MeSH

CatalysisKetonesLigandsOxidation-ReductionPalladium

Pub Type(s)

Journal Article

Language

eng

PubMed ID

34761844

Citation

Kudashev, Anton, and Olivier Baudoin. "Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 27, no. 70, 2021, pp. 17688-17694.
Kudashev A, Baudoin O. Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones. Chemistry. 2021;27(70):17688-17694.
Kudashev, A., & Baudoin, O. (2021). Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones. Chemistry (Weinheim an Der Bergstrasse, Germany), 27(70), 17688-17694. https://doi.org/10.1002/chem.202103467
Kudashev A, Baudoin O. Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones. Chemistry. 2021 Dec 15;27(70):17688-17694. PubMed PMID: 34761844.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones. AU - Kudashev,Anton, AU - Baudoin,Olivier, Y1 - 2021/11/11/ PY - 2021/09/23/received PY - 2021/11/12/pubmed PY - 2021/12/18/medline PY - 2021/11/11/entrez KW - C−H activation KW - arylation KW - palladium KW - site-selectivity SP - 17688 EP - 17694 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 27 IS - 70 N2 - A ligand-controlled site-selective C(sp3)-H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- to β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C-H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/34761844/Site_Selective_Pd_Catalyzed_C_sp3__H_Arylation_of_Heteroaromatic_Ketones_ DB - PRIME DP - Unbound Medicine ER -