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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.