Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
| Autor: | Bill Morandi, Philip Boehm, Tristano Martini, Yong Ho Lee, Bastien Cacherat |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
ligand non-innocence
Xantphos Iodide Phosphonium salt chemistry.chemical_element 010402 general chemistry 01 natural sciences Catalysis Reductive elimination chemistry.chemical_compound iodination Nucleophilic substitution Research Articles chemistry.chemical_classification 010405 organic chemistry Aryl General Chemistry Reaction Mechanism palladium Combinatorial chemistry 3. Good health 0104 chemical sciences chemistry shuttle catalysis Palladium Research Article |
| Zdroj: | Angewandte Chemie (International Ed. in English) Angewandte Chemie International Edition Angewandte Chemie. International Edition, 60 (31) |
| ISSN: | 1521-3773 |
| Popis: | 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. 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 was developed. 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. |
| Databáze: | OpenAIRE |
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