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Iron-Catalyzed SO-Retaining Smiles Rearrangement through Decarboxylation.
Org Lett
December 2024
Institute of Green Chemistry and Molecular Engineering, GBRCE for Functional Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou 510006, PR China.
Radical Smiles rearrangements have emerged as powerful methodologies for constructing carbon-carbon bonds through intramolecular radical addition and fragmentation under milder conditions, with SO released as a byproduct. However, SO-retaining Smiles rearrangements, which can yield valuable alkyl sulfone derivatives, have been scarcely explored. In this study, we present an unprecedented iron-catalyzed SO-retaining Smiles rearrangement initiated by the decarboxylation of aliphatic carboxylic acids.
View Article and Find Full Text PDFIron-Catalyzed Cross-Electrophile Coupling for the Formation of All-Carbon Quaternary Centers.
J Am Chem Soc
December 2024
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
Quaternary carbon centers are desirable targets for drug discovery and complex molecule synthesis, yet the synthesis of these motifs within traditional cross-coupling paradigms remains a significant challenge due to competing β-hydride elimination pathways. In contrast, the bimolecular homolytic substitution (S2) mechanism offers a unique and attractive alternative pathway. Metal porphyrin complexes have emerged as privileged catalysts owing to their ability to selectively form primary metal-alkyl complexes, thereby eliminating the challenges associated with tertiary alkyl complexation with a metal center.
View Article and Find Full Text PDFIron-Catalyzed Perfluoroalkylarylation of Styrenes with Arenes and Alkyl Iodides Enabled by Halogen Atom Transfer.
Org 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 PDFIntramolecular C-H Oxidation in Iron(V)-oxo-carboxylato Species Relevant in the γ-Lactonization of Alkyl Carboxylic Acids.
ACS Catal
September 2024
Institut de Química Computacional i Catàlisi (IQCC), Departament de Química, Universitat de Girona, C/Ma Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain.
High-valent oxoiron species have been invoked as oxidizing agents in a variety of iron-dependent oxygenases. Taking inspiration from nature, selected nonheme iron complexes have been developed as catalysts to elicit C-H oxidation through the mediation of putative oxoiron(V) species, akin to those proposed for Rieske oxygenases. The addition of carboxylic acids in these iron-catalyzed C-H oxidations has proved highly beneficial in terms of product yields and selectivities, suggesting the direct involvement of iron(V)-oxo-carboxylato species.
View Article and Find Full Text PDFEffective Alkyl-Alkyl Cross-Coupling with an Iron-Xantphos Catalyst: Mechanistic and Structural Insights.
Angew Chem Int Ed Engl
January 2025
Inorganic Chemistry Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QR, UK.
While iron-catalyzed C(sp)-C(sp) cross-couplings have been widely studied and developed in the last decade, alkyl-alkyl cross-coupling systems with iron remain underdeveloped despite the importance of C(sp)-C(sp) bonds in organic synthesis. A major challenge to the development of these reactions is the current lack of fundamental insight into ligand effects and organoiron intermediates that enable effective alkyl-alkyl couplings. The current study addresses this longstanding limitation using a combination of Fe Mössbauer spectroscopy, SC-XRD (single-crystal X-ray diffraction) and reactivity studies of alkyl-alkyl coupling with iron-Xantphos to define the in situ formed iron-Xantphos intermediates in catalysis.
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