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This paper describes an efficient [4 + 3] cycloaddition reaction of 3-indolylmethanols with cyclopentadiene in hexafluoroisopropanol (HFIP), which is catalyst-free and inexpensive, and offers mild reaction conditions, wide substrate scope and convenient workup. This methodology provides the first catalyst- and additive-free [4 + 3] cycloaddition reactions of indolyl alcohols, offering a green and efficient method for the synthesis of cyclohepta[b]indole derivatives.
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http://dx.doi.org/10.1039/c6ob01953f | DOI Listing |
J Org Chem
September 2025
Pharmaron Drug Discovery Services Europe, Pharmaron UK Ltd., West Hill Innovation Park, Hertford Road, Hoddesdon EN11 9FH, United Kingdom.
Sulfur(VI) fluoride exchange (SuFEx) compounds are gaining increasing attention due to their various applications. We present the Diels-Alder reaction of ethenesulfonyl fluoride and analogues to rapidly access cyclic and bicyclic SuFEx derivatives in moderate to good yields. These derivatives have been shown to be useful intermediates in a variety of synthetic transformations to expand the toolkit for the preparation of cyclic aliphatic sulfonyl fluorides.
View Article and Find Full Text PDFInorg Chem
September 2025
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130021, P. R. China.
The CO cycloaddition route is an effective way to achieve efficient conversion and utilization of CO. Zeolites with diverse topologies and tunable acidic sites can efficiently promote the cycloaddition reaction of CO with epoxides. The exchangeable cations in zeolites have a great influence on the performance of the CO cycloaddition, but there are few studies on it.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
Center of Drug Discovery, State Key Laboratory of Natural Medicine, China Pharmaceutical University, Nanjing 211198, China.
The advancement of bioorthogonal cleavage platforms has emerged as a critical frontier in chemical biology, offering precise molecular liberation through physiologically compatible activation mechanisms. Despite its significant potential, ensuring efficacy typically requires rapid reaction kinetics, high-efficiency payload release, and stable reactants; however, relevant reports remain sparse. Herein, we developed a strain-promoted alkyne-nitrone cycloaddition (SPANC)-based click-release chemistry through installation of a carbamate-linked release moiety at the propargyl position of cyclooctyne, triggering a spontaneous elimination following click cycloaddition to achieve efficient payload liberation.
View Article and Find Full Text PDFBeilstein J Nanotechnol
August 2025
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
The preparation of multimodal nanoparticles by capping magnetic iron oxide nanoparticles (IONPs) with functional organic molecules is a major area of research for biomedical applications. Conjugation reactions, such as carbodiimide coupling and the highly selective class of reactions known as "click chemistry", have been instrumental in tailoring the ligand layers of IONPs to produce functional biomedical nanomaterials. However, few studies report the controls performed to determine if the loading of molecules onto IONPs is due to the proposed coupling reaction(s) employed, or some other unknown interaction with the IONP surface.
View Article and Find Full Text PDFRSC Adv
September 2025
Process and Environmental Engineering Laboratory (LIPE), Faculty of Chemistry, University of Science and Technology of Oran Mohamed Boudiaf P. O. Box 1503, El Mnaouer 31000 Oran Algeria.
In this contribution, Molecular Electron Density Theory (MEDT) is employed to investigate the (3 + 2) cycloaddition reaction between ()--methyl--(2-furyl)-nitrone 1 and but-2-ynedioic acid 2. DFT calculations at the M06-2X-D3/6-311+G(d,p) level of theory under solvent-free conditions at room temperature show that this reaction proceeds CA3-Z diastereoselectivity, with the formation of the CA3-Z cycloadduct being both thermodynamically and kinetically more favoured than the CA4-Z one. Reactivity parameters obtained from CDFT calculations reveal that compound 1 predominantly behaves as a nucleophile with moderate electrophilic features, in contrast to compound 2, which demonstrates strong electrophilicity and limited nucleophilic ability.
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