4.7 Article

Deuterodechlorination of Aryl/Heteroaryl Chlorides Catalyzed by a Palladium/Unsymmetrical NHC System

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 19, Pages 8934-8946

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01609

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Funding

  1. JSPS
  2. MEXT KAKENHI [15K07862, 26105746]
  3. Takeda Science Foundation
  4. Grants-in-Aid for Scientific Research [26105746, 15K07862, 16K08167] Funding Source: KAKEN

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The catalytic deuterodechlorination of aryl/heteroaryl chlorides was developed with a palladium/unsymmetrical NHC system, and the precisely controlled introduction of deuterium into a variety of aryl/heteroaryl compounds was achieved with a high level of efficiency, selectivity, and deuteration degree. This method was also successfully applied to the transformation of bioactive agents even in a gram-scale synthesis. The crystal structure analysis of Pd-HC complexes led to the observation of Pd-arene interaction.

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