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Herein, a metal-free and versatile strategy was successfully reported for the divergent synthesis of various functionalized dibenzo[,]selenophenes, dibenzo[,]tellurophenes, and phenoxaselenines in moderate to excellent yields in one-pot. This method utilized commercially available, cheap, and sustainable ammonium bromide as the catalyst to promote the radical cyclization of biarylboronic acids with elemental Se/Te. Comparatively, this method was highlighted by its readily available starting material, broad substrate scope, simple catalytic system, easy operation, good safety, being strongly oxidant-free, and easily scalable. The preliminary mechanistic experiments suggested that this transformation could possibly proceed via a radical pathway.
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http://dx.doi.org/10.1021/acs.joc.5c01441 | DOI Listing |
Org Biomol Chem
September 2025
Research Centre of Modern Analytical Technology, Tianjin University of Science & Technology, Tianjin 300457, China.
A tetrahydroxydiboron-mediated radical cyclization of unactivated alkenes under photoinduced reaction conditions was developed to synthesize ring-fused quinazolinones for the first time. The concise, mild and photocatalyst- and oxidant-free conditions, as well as the good functional group tolerance, render this protocol a green and convenient strategy for synthesizing polycyclic ring-fused quinazolinones. Mechanistic studies indicated that the process might involve a radical pathway.
View Article and Find Full Text PDFJ Org Chem
September 2025
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061, China.
A visible-light-induced cascade cyclization of isocyanobiaryls with hydrosilanes has been developed for the synthesis of 6-silylated phenanthridines. Readily available hydrosilanes were employed as silyl radical precursors under room-temperature conditions. The merits of the transformation include operational simplicity, mild conditions, high atom economy, and good functional group compatibility.
View Article and Find Full Text PDFOrg 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.
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