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. Without a trace: Carboxylic acids are used as traceless directing groups in the Ir-catalyzed direct C-H amidation of arenes with sulfonyl azides under mild conditions. The tandem protodecarboxylation of the ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)anilines, which are difficult to obtain by other C-H functionalization approaches.
Lee, Donggun,Chang, Sukbok
p. 5364 - 5368
(2015/03/30)
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