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A direct sp3 C-H amination of cyclic amines (dihydroquinoxalinones and dihydrobenzoxazinones) with dialkyl azo dicarboxylates accelerated by visible-light irradiation under metal and photocatalyst-free conditions is described. This protocol features very mild reaction conditions for the synthesis of aminal quinoxaline and benzoxazine derivatives with good to high yields (up to 99%). These aminal derivatives respresent versatile building blocks for the divergent synthesis of quinoxalin-2-one derivatives.
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http://dx.doi.org/10.1039/d1ob01157j | DOI Listing |
Org Lett
September 2025
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
A visible-light-induced decarbonylation/Truce-Smiles rearrangement cascade has been developed for the direct synthesis of 2-aminobenzophenones. This protocol employs readily available isatins and sulfonyl chlorides as starting materials, enabling the construction of diverse 2-aminobenzophenone derivatives under mild conditions without the need for transition metal catalysts or photocatalysts. The reaction exhibits a broad substrate scope, excellent functional group tolerance, and high efficiency.
View Article and Find Full Text PDFOrg Biomol Chem
September 2025
Organic Synthesis Laboratory, P. G. Department of Chemistry, Berhampur University, Bhanja Bihar, Odisha, 760007, India.
Herein, we report a visible light-mediated, metal- and photocatalyst-free, green and sustainable synthesis of biologically relevant functionalized benzopyrans by a one-pot, pseudo-multicomponent reaction at room temperature. The notable features of the present protocol include a green and renewable energy source, high yields, easy isolation of the products without performing column chromatography, metal- and photocatalyst-free conditions, room-temperature synthesis, broad substrate scope, environmental friendliness and gram-scale synthesis of the products. In the present study, the benzopyrans are also subjected to molecular docking, which revealed that some benzopyrans are promising potential inhibitors of key nsPs in both Chikungunya and Zika viruses.
View Article and Find Full Text PDFOrg Lett
August 2025
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China.
Herein, we report a visible-light-induced α-trifluoromethylation of α,β-unsaturated carbonyl compounds using Langlois reagent (CFSONa) as the trifluoromethyl source and pyruvic acid () as an additive. This metal- and photocatalyst-free protocol exhibits a broad substrate scope, affording the desired products in isolated yields ranging from 34% to 79%. This method was further applied to the synthesis of LTZ-8, a drug candidate for benign prostatic hyperplasia (BPH).
View Article and Find Full Text PDFOrg Lett
August 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Bicyclo[1.1.0]butanes (BCBs) are activated using photocatalysts, Lewis and Brønsted acids, transition metal catalysts, and more recently hexafluoroisopropanol (HFIP).
View Article and Find Full Text PDFAcc Chem Res
August 2025
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
ConspectusThe strategic implementation of asymmetric catalytic radical reactions has evolved into a sophisticated methodology for constructing stereogenic centers, driven by remarkable advancements in radical generation techniques. However, achieving high stereoselectivity remains a formidable challenge due to the inherent high reactivity, transient lifetime of radical species, and presence of competing racemic background pathways. Addressing these limitations necessitates precise catalytic systems capable of orchestrating radical generation and enantioselective transformation in a controlled manner.
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