589-87-7Relevant articles and documents
Acidic ionic liquid supported on silica-coated magnetite nanoparticles as a green catalyst for one-pot diazotization-halogenation of the aromatic amines
Isaad, Jalal
, p. 49333 - 49341 (2014)
Acidic ionic liquid was immobilized on silica-coated magnetite nanoparticles (Fe3O4@SILnP) and used as an efficient heterogeneous catalyst for the diazotization-iodination reaction of different aromatic amines under solvent-free conditions at room temperature. The diazonium salts that are formed by this catalyst are stable at room temperature and react rapidly with sodium iodide to produce aryl iodides in good to excellent yields. This method has some advantages such as low pollution, rapid access to products, simple work-up and easy separation of catalyst from the reaction mixture.
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information, p. 17211 - 17217 (2021/07/02)
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska
supporting information, p. 18717 - 18722 (2020/08/25)
While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.