Ru-Catalyzed C(sp2)-H Bond Arylation of Benzamides Bearing a Novel 4-Aminoantipyrine as a Directing Group

A novel design-based removable N,O-bidentate directing group based on cheap and commercially available 4-aminoantipyrine (AAP) is reported. Aromatic AP amides bearing 4-aminoantipyrine underwent efficient Ru-catalyzed C(sp(2))-H arylation using [RuCl2(PPh3)(3)] as a catalyst and aryl bromides as electrophiles. The novel bidentate directing group enabled the C-H functionalization reaction with good scope, good functional group tolerance and in decent yields.

Automated summary

The novel design-based removable N,O-bidentate directing group enabled efficient Ru-catalyzed C(sp(2))-H arylation using 4-aminoantipyrine as a cheap and commercially available starting material. The reaction exhibited good scope, good functional group tolerance, and decent yields.