We herein reported a novel photoredox-catalyzed three-component alkylarylation of vinyl arenes with alkylboronic pinacol esters (APEs) and cyanoarenes via radical addition/cross-coupling to construct 1,1-diarylalkanes. In this transformation, alkyl radicals were easily available by visible-light-induced oxidative N-H cleavage of morpholine, which used APEs as a radical precursor. Furthermore, this protocol exhibited a broad substrate scope, enabling various styrenes, APEs, and cyanoarenes, as well as bioactive molecule derivatives.
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http://dx.doi.org/10.1021/acs.orglett.4c02335 | DOI Listing |
J Org Chem
January 2025
College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, P. R. China.
Herein, we present a copper-catalyzed, three-component intermolecular 1,4-alkylarylation of 1,3-enynes with ethers and aryl boronic acids. This method, driven by α-C(sp)-H functionalization of the oxygen atom in ethers, regioselectively produces various tetrasubstituted allenes from simple, readily available precursors. Key features include mild reaction conditions and a simple catalytic system.
View Article and Find Full Text PDFJ Org Chem
December 2024
Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), 1037 Luoyu Road, Wuhan 430074, P. R. China.
Recently, metallaphotoredox-catalyzed alkene dicarbofunctionalization reactions have been extensively investigated. Most cases are related to alkyl-arylation processes by conjugate coupling of alkyl radical precursors and aryl electrophiles across alkenes. By contrast, reported examples of alkylvinylation by coupling of vinyl electrophiles are largely limited.
View Article and Find Full Text PDFOrg Lett
November 2024
Key Laboratory of Jiangxi Province for Persistent Pollutants Prevention Control and Resource Reuse, Nanchang Hangkong University, Nanchang 330063, China.
A new iron-catalyzed three-component perfluoroalkylarylation of styrenes with alkyl halides and arenes has been established. Alkyl halides undergo halogen atom transfer with methyl radicals to form alkyl radicals in reactions initiated by a combination of -butyl peroxybenzoate and an iron catalyst, thus adducting to the olefins, which results in alkylarylation products. The protocol is compatible with a wide range of perfluoroalkyl and non-perfluoroalkyl halides, features excellent functional group tolerance, and enables the synthesis of structurally diverse 1,1-diaryl fluoro-substituted alkanes.
View Article and Find Full Text PDFOrg Biomol Chem
August 2024
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, 214122, China.
Visible-light-induced three-component 1,2-alkyl-arylation of alkenes and alkyl radical addition/cyclization of acrylamides have been realized a photocatalytic halogen-atom transfer (XAT) process. This metal-free protocol utilizes readily available tertiary alkylamine as both an electron donor and an XAT reagent for the activation of alkyl halides using naphthalimide (NI)-based organic photocatalysts. This process features broad substrate scope and good functional group tolerance under mild conditions, and could be effectively applied to a variety of medicinally relevant substrates.
View Article and Find Full Text PDFOrg Lett
August 2024
School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, China.
We herein reported a novel photoredox-catalyzed three-component alkylarylation of vinyl arenes with alkylboronic pinacol esters (APEs) and cyanoarenes via radical addition/cross-coupling to construct 1,1-diarylalkanes. In this transformation, alkyl radicals were easily available by visible-light-induced oxidative N-H cleavage of morpholine, which used APEs as a radical precursor. Furthermore, this protocol exhibited a broad substrate scope, enabling various styrenes, APEs, and cyanoarenes, as well as bioactive molecule derivatives.
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