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A Pd-mediated C-H activation methodology was developed for the direct arylation of quinoidal skeletons, both by means of homogeneous catalysis and heterogeneous catalysis using metal-decorated carbon nanotubes, enabling the direct functionalization of quinones in moderate to excellent yields. The derivatives obtained were tested against trypomastigote forms of , showing promising biological activity.
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http://dx.doi.org/10.1021/acsomega.5c05006 | DOI Listing |
ACS Omega
August 2025
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil.
A Pd-mediated C-H activation methodology was developed for the direct arylation of quinoidal skeletons, both by means of homogeneous catalysis and heterogeneous catalysis using metal-decorated carbon nanotubes, enabling the direct functionalization of quinones in moderate to excellent yields. The derivatives obtained were tested against trypomastigote forms of , showing promising biological activity.
View Article and Find Full Text PDFChem Commun (Camb)
April 2024
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
An efficient Rh(II)-catalyzed highly selective -arylation of benzotriazole, indazole, and 1,2,3 triazole is developed using diazonaphthoquinone. The developed protocol is extended with a wide scope. In addition, late-stage arylation of these scaffolds tethered with bioactive molecules is explored.
View Article and Find Full Text PDFOrg Lett
April 2023
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
A Rh(II)-catalyzed simple and efficient synthesis of -arylated 2-pyridone derivatives is described using 2-oxypyridine and diazonaphthoquinone as coupling partners. The reaction proceeds through the insertion of the nitrogen atom of the 2-oxypyridine derivative into quinoid carbene and subsequent 1,6-benzoyl migratory rearrangement. The reaction is broadened with sufficient scope and has the potential to offer axially chiral -arylated 2-pyridone derivatives under suitable asymmetric conditions.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2022
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071, China.
Diarylamines and related scaffolds are ubiquitous atropisomeric chemotypes in biologically active natural products. However, the catalytic asymmetric synthesis of these axially chiral compounds remains largely unexplored. Herein, we report that a BINOL-derived chiral phosphoric acid (CPA) successfully catalyzed the atroposelective coupling of quinone esters and anilines through direct C-N bond formation to afford N-aryl quinone atropisomers with an unprecedented intramolecular N-H-O hydrogen bond within a six-membered ring in good yields and enantioselectivities with the quinone ester as both the electrophile and the oxidant.
View Article and Find Full Text PDFJ Am Chem Soc
March 2022
School of Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi Province 710049, People's Republic of China.
A series of novel terphenylene viologen derivatives (TPV) with through-space conjugation (TSC) via the combination of terphenylene skeletons with viologen structure is reported. Their optoelectronic properties can be adjusted by -arylation or -alkylation reactions. Compared with other viologen derivatives, TPV not only exhibits strong photoluminescence but also retards the charge recombination process and stabilizes the diradical state without forming a quinoid structure due to the special TSC effect.
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