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

Yue Huifeng | Zendy; Guo Lin | Zendy; Lee ShaoChi | Zendy; Liu Xiangqian | Zendy; Rueping Magnus | Zendy

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

Author(s) -

Yue Huifeng,

Guo Lin,

Lee ShaoChi,

Liu Xiangqian,

Rueping Magnus

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201612624

Subject(s) - amide , chemistry , catalysis , aryl , nickel , combinatorial chemistry , functional group , reductive elimination , molecule , organic chemistry , carboxylic acid , alkyl , polymer

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.

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