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Direct CH Amidation of Benzoic Acids to Introduce meta ‐ and para ‐Amino Groups by Tandem Decarboxylation
Author(s) -
Lee Donggun,
Chang Sukbok
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500331
Subject(s) - decarboxylation , sulfonyl , chemistry , aniline , benzoic acid , tandem , functional group , combinatorial chemistry , surface modification , organic chemistry , aniline compounds , catalysis , materials science , alkyl , polymer , composite material
The Ir‐catalyzed mild CH amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional‐group compatibility. Subsequent protodecarboxylation of ortho ‐amidated benzoic acid products afforded meta ‐ or para ‐substituted ( N ‐sulfonyl)aniline derivatives, the latter being inaccessible by other CH functionalization approaches. The decarboxylation step was compatible with the amidation conditions, enabling a convenient one‐pot, two‐step process.