Monodentate Transient Directing Group Assisted Ruthenium(II)-Catalyzed
Direct ortho-C–H Imidation of Benzaldehydes
for Diverse Synthesis of Quinazoline and Fused Isoindolinone
posted on 2021-05-03, 14:34authored byYongdi Wu, Na Liu, Meifang Qi, Huihao Qiao, Xuelian Lu, Li Ma, Yirong Zhou, Fang-Lin Zhang
2-Fluoro-5-(trifluoromethyl)aniline
was found to be a suitable
monodentate transient directing group (MonoTDG) to enable Ru(II)-catalyzed
intermolecular direct ortho-C(sp2)–H
imidation of benzaldehydes. N-Tosyloxyphthalimide
was used as an alternative azide-free amidation reagent to achieve
high efficiency and good functional group tolerance. Moreover, the
reaction could be enlarged to gram scale, and the amidated product
could be readily converted into useful quinazoline and fused isoindolinone
scaffolds by one-step derivatization.