4.8 Article

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

Journal

ORGANIC LETTERS
Volume 23, Issue 20, Pages 8098-8103

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03232

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Funding

  1. Shandong Lunan Coal Chemical Research Institute of Engineering and Technology, Zaozhuang University
  2. Zaozhuang Science and Technology Development Program [2018GH19]
  3. NSF [CHE-1650766]
  4. Rutgers University
  5. Nanjing University of Information Science and Technology

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The Pd-catalyzed double-decarbonylative synthesis of aryl thioethers involves an aryl exchange reaction between amides and thioesters, with amides serving as aryl donors and thioesters as sulfide donors. The use of Pd/Xantphos without any additives promotes aryl exchange by C(O)-N/C(O)-S cleavages, allowing for a wide variety of amides and sulfides to be used in the reaction.
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.

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