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Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

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Lee,  Yong Ho
Laboratorium für Organische Chemie, ETH Zürich;
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cacherat,  Bastien
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Laboratorium für Organische Chemie, ETH Zürich;
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Boehm, P., Martini, T., Lee, Y. H., Cacherat, B., & Morandi, B. (2021). Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange. Angewandte Chemie International Edition, 60(31), 17211-17217. doi:10.1002/anie.202103269.


Cite as: https://hdl.handle.net/21.11116/0000-0008-EEA6-1
Abstract
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.