4.8 Article

Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

Journal

ACS CATALYSIS
Volume 11, Issue 21, Pages 13217-13222

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c04183

Keywords

difunctionalization; isocyanide; radical; palladium; light-induced

Funding

  1. National Institutes of Health [GM120281]
  2. National Science Foundation [CHE-1955663]
  3. Welch Foundation [AT-0041]

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A novel reaction method has been developed for visible light-induced alkyl-carbamoylation and cyanation of alkenes, leading to the synthesis of amides and nitriles. This method is highly efficient and versatile, allowing for the rapid construction of a wide range of valuable compounds.
A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.

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