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

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.

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 Creators:
Boehm, Philip1, Author
Martini, Tristano1, Author
Lee, Yong Ho1, 2, Author              
Cacherat, Bastien2, Author              
Morandi, Bill1, 2, Author              
Affiliations:
1Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, ou_persistent22              
2Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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Free keywords: iodination; ligand non-innocence; palladium; reaction mechanism; shuttle catalysis
 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.

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Language(s): eng - English
 Dates: 2021-03-052021-05-192021-07-26
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202103269
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (31) Sequence Number: - Start / End Page: 17211 - 17217 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851