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.