Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

H. Yue, L. Guo, S.-C. Lee, X. Liu, M. Rueping
Angew. Chem. Int. Ed., 56, 39-72, (2017)

Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

Keywords

Arenes, Heteroarenes, Nickel-Catalyzed CO and CN Bond Activation

Abstract

​An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.

Code

DOI: 10.1002/anie.201612624

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