A simple and inexpensive system comprised of H(2)O(2)-pyridine-FeCl(3)·6H(2)O for the catalysis of olefin epoxidation was established. Intriguingly, the reactivity of this system greatly depends on the amounts of pyridine. Various substrates, including aromatic and aliphatic olefins, were epoxidized by this simple system in moderate to excellent yields.
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http://dx.doi.org/10.1248/cpb.59.799 | DOI Listing |
Org Lett
January 2025
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
Simple aryl chlorides represent challenging substrates in iron-catalyzed borylation. A combination of Li[B(Bu)pin-Bpin] as the borylating reagent and a catalyst formed in situ from iron(II) triflate and the commercially available N-heterocyclic carbene ligand, IMes, gives significantly improved activity and a much broader scope than previously reported iron-based catalysts. Iron triflate is also a good precatalyst for the borylation of aryl triflates─a previously unreported transformation─and in these cases the IMes ligand is not required.
View Article and Find Full Text PDFJ Org Chem
December 2024
School of Chemical and Environmental Engineering, Hunan Institute of Technology, Hengyang 421002, China.
An iron-catalyzed oxidative [3 + 3] annulation of oxime esters with inactivated saturated ketones is described. This cascade strategy allows one-step rapid synthesis of various structurally important pyridines through an oxidative dehydrogenation/annulation/oxidative aromatization sequence via direct α,β-dehydrogenation of simple saturated ketones followed by annulation with oximes. This method shows good functional group tolerance, readily accessible starting materials, a wide substrate scope, high chemoselectivity, and no need for extra stoichiometric oxidant and is also applicable to the late-stage functionalization of natural products.
View Article and Find Full Text PDFJ Org Chem
October 2024
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, United Kingdom.
Herein, we report an iron-catalyzed transfer hydrogenation of allylic alcohols. The operationally simple protocol employs a well-defined bench stable (cyclopentadienone)iron(0) carbonyl complex as a precatalyst in combination with KCO (4 mol %) and isopropanol as the hydrogen donor. A diverse range of allylic alcohols undergo transfer hydrogenation to form the corresponding alcohols in good yields (33 examples, ≤83% isolated yield).
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
International Joint Laboratory on Resource Chemistry, Shanghai Normal University, 200234, Shanghai, P. R. China.
The development of a mechanochemical Fe-catalyzed Wacker oxidation of olefins with a sustainable and benign procedure holds significant promise for industrial applications. However, navigating the intricate interactions inherent in ball-milling conditions to fine-tune reaction selectivity remains a formidable challenge. Herein, leveraging the dispersive and/or trapping properties of cyclodextrins, an innovative mechanochemical approach is developed through the integration of cyclodextrins into a Fe-catalyzed system, enabling a streamlined Wacker oxidation process from simple and/or commercially available alkenes.
View Article and Find Full Text PDFOrg Lett
August 2024
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, China.
Herein, we describe a novel photoinduced iron-catalyzed strategy for multicomponent C-H alkylation of in situ generated imines. By utilizing the alkyl radicals generated through iron-mediated photocatalytic C-H activation, the imines formed in situ are further subjected to addition reactions, resulting in the synthesis of various secondary and tertiary amine products. This method is simple to operate and does not require additional oxidants.
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