Direct C-H amidation of benzoic acids to introduce meta- and para-amino groups by tandem decarboxylation.

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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Donggun Lee, Sukbok Chang. Direct C-H amidation of benzoic acids to introduce meta- and para-amino groups by tandem decarboxylation. Chemistry (Weinheim an der Bergstrasse, Germany). 2015 Mar 27;21(14):5364-8

PMID: 25688935

search → result