Monodentate Transient Directing Group Assisted Ruthenium(II)-Catalyzed Direct <i>ortho</i>-C–H Imidation of Benzaldehydes for Diverse Synthesis of Quinazoline and Fused Isoindolinone
Yongdi Wu, Na Liu, Mei-Fang Qi, Huihao Qiao, Xuelian Lu, Li Ma, Yirong Zhou, Fang‐Lin Zhang
Abstract
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.
Topics & Concepts
ChemistryQuinazolineCatalysisAnilineReagentCombinatorial chemistryDenticityFunctional groupDerivatizationRutheniumAzideIntermolecular forceOrganic chemistryMoleculeCrystal structureHigh-performance liquid chromatographyPolymerCatalytic C–H Functionalization MethodsQuinazolinone synthesis and applicationsSynthetic Organic Chemistry Methods