Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation
KAUST DepartmentPhysical Sciences and Engineering (PSE) Division
Chemical Science Program
KAUST Catalysis Center (KCC)
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AbstractAn 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.
CitationYue H, Guo L, Lee S-C, Liu X, Rueping M (2017) Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation. Angewandte Chemie International Edition 56: 3972–3976. Available: http://dx.doi.org/10.1002/anie.201612624.
SponsorsH.Y. and L.G. acknowledge the China Scholarship Council. Support by King Abdullah University of Science and Technology (KAUST) is gratefully acknowledged.