@article{7bc1e85605d44eeaa4c7592425700bbd,
title = "Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange",
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.",
keywords = "iodination, ligand non-innocence, palladium, reaction mechanism, shuttle catalysis",
author = "Philip Boehm and Tristano Martini and Lee, {Yong Ho} and Bastien Cacherat and Bill Morandi",
note = "Funding Information: This project received funding from the European Research Council under the European Union's Horizon 2020 research and innovation program (Shuttle Cat, Project ID: 757608), the FCI (scholarship to P.B.), LG Chem (scholarship to Y.H.L.), ETH Z{\"u}rich, the Max‐Planck‐Society, and the Max‐Planck‐Institut f{\"u}r Kohlenforschung. We thank the NMR service, the Molecular and Biomolecular Analysis Service (MoBiAS), and X‐ray (SMoCC) service of ETH Z{\"u}rich for assistance. We thank Marius Lutz and Miguel Rivero Crespo for assistance with the kinetic studies and our group for critical proofreading of the manuscript. Funding Information: This project received funding from the European Research Council under the European Union's Horizon 2020 research and innovation program (Shuttle Cat, Project ID: 757608), the FCI (scholarship to P.B.), LG Chem (scholarship to Y.H.L.), ETH Z?rich, the Max-Planck-Society, and the Max-Planck-Institut f?r Kohlenforschung. We thank the NMR service, the Molecular and Biomolecular Analysis Service (MoBiAS), and X-ray (SMoCC) service of ETH Z?rich for assistance. We thank Marius Lutz and Miguel Rivero Crespo for assistance with the kinetic studies and our group for critical proofreading of the manuscript. Publisher Copyright: {\textcopyright} 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH",
year = "2021",
month = jul,
day = "26",
doi = "10.1002/anie.202103269",
language = "English",
volume = "60",
pages = "17211--17217",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "31",
}