American Chemical Society
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Monodentate Transient Directing Group Assisted Ruthenium(II)-Catalyzed Direct ortho-C–H Imidation of Benzaldehydes for Diverse Synthesis of Quinazoline and Fused Isoindolinone

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journal contribution
posted on 2021-05-03, 14:34 authored by Yongdi 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.