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A domino Cu-catalyzed nucleophilic cyclization and C-C bond activation to access various 3-acylated benzofurans has been developed. The generated benzofuranylcopper intermediate was coupled with cyclopropenone, wherein the ring-opening of cyclopropenone with phenol was effectively suppressed. This strategy features excellent substrate scope, good functional group tolerance, and high atomic economy.
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http://dx.doi.org/10.1039/d5cc01764e | DOI Listing |
Chem Commun (Camb)
September 2025
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
A CFOH-catalysed tandem cyclization of -alkynylnaphthols and -quinone monoketals is disclosed. The CFOH catalyst activates alkynylnaphthol to generate an all-carbon tetrasubstituted VQM by nucleophilic addition to quinone monoketal (Michael addition). Furthermore, the CFOH catalyst triggers -quinone monoketal to generate an electrophilic oxocarbenium cation to be captured by -alkynylnaphthol regiospecifically, resulting in the formation of an all-carbon tetrasubstituted VQM, followed by an intramolecular cyclization to afford a series of 1-(3-arylbenzofuran-2-yl)naphthalen-2-ols.
View Article and Find Full Text PDFChem Commun (Camb)
September 2025
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710127, China.
A domino Cu-catalyzed nucleophilic cyclization and C-C bond activation to access various 3-acylated benzofurans has been developed. The generated benzofuranylcopper intermediate was coupled with cyclopropenone, wherein the ring-opening of cyclopropenone with phenol was effectively suppressed. This strategy features excellent substrate scope, good functional group tolerance, and high atomic economy.
View Article and Find Full Text PDFMolecules
August 2025
Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague, Czech Republic.
The stereoselective synthesis of trisubstituted alkenes has become a key topic in modern organic chemistry. At the same time, trisubstituted alkenes also serve as valuable starting materials for a wide range of transformations. However, it remains unclear to what extent these alkenes are utilized in comparison to their mono- and disubstituted counterparts.
View Article and Find Full Text PDFAcc Chem Res
August 2025
Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
ConspectusAlkynes are one of the most fundamental functional groups in organic synthesis due to the versatile chemistry of the triple bond, their unique rigid structure, and their use in bioconjugation. The introduction of alkynes onto organic molecules traditionally relies on nucleophilic activation, often requiring strong bases or metal catalysts. These conditions, however, restrict applications involving biomolecules such as peptides and proteins due to functional group incompatibility.
View Article and Find Full Text PDFMed Chem
August 2025
Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam, Tirupati, Andhra Pradesh, India.
Introduction: Despite significant progress in cancer treatment, the need for new anticancer agents remains critical. Current research efforts are directed toward discovering novel compounds that exhibit potent cytotoxic activity while minimizing adverse effects. Thus, tetrazole derivatives have gained attention due to their potential biological activities, including anticancer effects.
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