title: Direct C-H amidation of benzoic acids to introduce meta- and para-amino groups by tandem decarboxylation.
abstract: The Ir-catalyzed mild C-H 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 C-H functionalization approaches. The decarboxylation step was compatible with the amidation conditions, enabling a convenient one-pot, two-step process.
authors: Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701 (Republic of Korea); Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305-701 (Republic of Korea).
authors: Donggun
authors: D
authors: Lee
authors: Sukbok
authors: S
authors: Chang
mesh_terms: D000577:Amides / Q000737:chemistry*; D000586:Amination; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000577:Amides; D000814:Aniline Compounds; D001386:Azides; D001565:Benzoates; D013457:Sulfur Compounds; C023650:aniline
keywords: CH amidation; decarboxylation; meta- and para-substituted anilines; tandem processes; traceless directing groups