An efficient and sustainable approach for the synthesis of 2,4-diarylquinolines has been developed via a visible-light-promoted metal-free three-component decarboxylative annulation pathway. This one-pot protocol combines readily available feed-stock α,β-unsaturated acids, aromatic amines, and α-keto acids in a cascade manner to access substituted quinolines under eco-benign conditions. Moreover, mechanistic insights suggest initial C-C cross coupling followed by decarboxylative 6π electrocyclic annulation to afford the desired products. The broad substrates scope and excellent functional group tolerance make this protocol more attractive and synthetically applicable toward the construction of complex -heterocycles.
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http://dx.doi.org/10.1021/acs.orglett.5c00099 | DOI Listing |
Chem Commun (Camb)
March 2025
Key Laboratory of Syngas Conversion of Shaanxi Province, Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
C-H functionalization provides an efficient route to construct complex organic molecules. The introduction of directing groups enhances the site-selectivity of the reaction. Carboxyl as a directing group can be easily transformed into other functional groups afterwards.
View Article and Find Full Text PDFOrg Lett
February 2025
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata, West Bengal 700032, India.
An efficient and sustainable approach for the synthesis of 2,4-diarylquinolines has been developed via a visible-light-promoted metal-free three-component decarboxylative annulation pathway. This one-pot protocol combines readily available feed-stock α,β-unsaturated acids, aromatic amines, and α-keto acids in a cascade manner to access substituted quinolines under eco-benign conditions. Moreover, mechanistic insights suggest initial C-C cross coupling followed by decarboxylative 6π electrocyclic annulation to afford the desired products.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, China.
Herein, we reported a sustainable and simple method involving electrochemical-catalyzed decarboxylative annulation and hydroaminomethylation of cyclic aldimines with -arylglycines by switching the reaction solvents. When the reaction was carried out in MeCN/HO or HO, the resulting products included imidazolidine-fused sulfamidates and C4-aminomethylated cyclic aldimines, obtained in moderate to good yields, respectively. Mechanistically, a radical pathway was proposed to be involved in this approach.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, India.
Chem Sci
January 2025
Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University Yanxiang Road 99 Xi'an 710045 China
The first Ni-catalyzed asymmetric decarboxylative strategy for the construction of carbocycles with contiguous quaternary all-carbon stereocenters is reported. The key to the success of these reactions is the utilization of rationally designed allenylic methylene cyclic carbonates as substrates with Ni catalysis. The floppy allenylic group exerts unique electronic properties on the carbonate, which allows further asymmetric nucleophilic annulations with alkenes.
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