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Radical cyclization has been demonstrated to be an efficient method to access functionalized heterocycles from easily accessible raw materials. Described herein is the development of a photocatalytic proton-coupled electron transfer (PCET) strategy for the synthesis of isoquinoline-1,3-diones using readily prepared naphthalimide (NI)-based organic photocatalysts. The process features free metal-complex photocatalysts, acids, and mild reaction conditions. This mild radical cyclization protocol has a broad substrate scope and can be effectively applied to a variety of medicinally relevant substrates. Furthermore, control experiments were conducted to elucidate the mechanism of this visible light-induced methodology.
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http://dx.doi.org/10.1021/acs.joc.4c00282 | DOI Listing |
Org Lett
September 2025
Department of Chemistry, University of Helsinki, 00014 Helsinki, Finland.
Visible-light-excited 3,6-bis(trifluoromethyl)-9,10-phenanthrenequinone (PQ-CF*) was used as a photocatalyst in the synthesis of 3-substituted -pyridyl indoles via cyclization of 2-vinylarylamines, where the photocatalyst was catalytically regenerated with the chloro(pyridine)cobaloxime complex. The versatility of the reaction was shown with 22 substrates providing up to 83% yields. Based on the mechanistic studies, we propose that PQ-CF directly activates the N-H bond, generating a nitrogen-centered aminyl radical as the key intermediate.
View Article and Find Full Text PDFRSC Adv
August 2025
Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences Tehran Iran
Indolo/benzimidazo-isoquinoline scaffolds are frequently found in many natural products, pharmaceuticals, and organic materials. Owing to their prominent properties, in recent years, numerous studies have been performed on the synthesis of indolo/benzimidazo-isoquinoline derivatives photo-, and electro-promoted functionalization/cyclization reactions of -acryloyl 2-aryl indoles/benzimidazoles. In this review, we describe these fascinating transformations and discuss their mechanistic insights.
View Article and Find Full Text PDFAs humanity ventures beyond Earth, developing radiation-stable coatings from non-fossil sources becomes essential. Beta radiation can significantly harm materials, making it essential to seek resilient, biobased alternatives to work in corrosive environments and high temperatures. Herein, a novel lignin-based coating demonstrating exceptional beta-radiation resistance and anticorrosion properties is presented.
View Article and Find Full Text PDFJ Mol Model
September 2025
School of Mechanical Engineering and Automation, Fuzhou University, Fuzhou, 350116, People's Republic of China.
Context: This study systematically investigates the growth mechanism of nitrogen-doped graphene in a plasma environment, with a particular focus on the effects of temperature and hydrogen radicals on its structural evolution. The results reveal that, at 3000 K, the formation of nitrogen-doped graphene proceeds through three stages: carbon chain elongation, cyclization, and subsequent condensation into planar structures. During this process, nitrogen atoms are gradually incorporated into the carbon network, forming various doping configurations such as pyridinic-N, pyrrolic-N, and graphitic-N.
View Article and Find Full Text PDFOrg Lett
September 2025
Precise Synthesis and Function Development Key Laboratory of Sichuan Province, China West Normal University, Nanchong, 637002, China.
A novel strategy for accessing unprecedented silyl/fluoroalkyl-embedded tetracyclic pyrrolizidinediones has been developed through the visible-light-induced cascade cyclization of 3-methyleneisoindolin-1-ones using hydrosilanes or fluoroalkylsulfinate salts as radical sources under redox-neutral conditions. This protocol features mild reaction conditions, operational simplicity, and excellent compatibility with various functional groups. A number of silyl/fluoromethyl-decorated tetracyclic pyrrolizidinedione frameworks were efficiently created.
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