Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester chemoselective C(acyl)-O bond activation

A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation via C(acyl)-O bond activation of est...

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Bibliographic Details
Published inRSC advances Vol. 9; no. 3; pp. 17266 - 17272
Main Authors Ma, Hongpeng, Bai, Chaolumen, Bao, Yong-Sheng
Format Journal Article
LanguageEnglish
Published 03.06.2019
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Summary:A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation via C(acyl)-O bond activation of esters by successful suppression of the undesired decarbonylation phenomenon. The catalyst can be reused and shows high activity after eight cycles. The XPS analysis of the catalyst before and after the reaction suggested that the reaction might be performed via a Pd 0 /Pd II catalytic cycle that began with Pd 0 . A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed.
Bibliography:Electronic supplementary information (ESI) available: GC-MS analysis of model reaction, characterization data for the products
1
H NMR and
13
C NMR spectra of the products. See DOI
10.1039/c9ra02394a
ISSN:2046-2069
DOI:10.1039/c9ra02394a