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Quinazoline-Assisted ortho-Halogenation with N-Halosuccinimides through Pd(II)-Catalyzed C(sp2)−H Activation

Yong Wang,Hui Wang,Qifan Yang,Shihua Xie,Hongjun Zhu

Graphical Herein, palladium(II)-catalyzed halogenation of 2-phenylquinazolines using N -halosuccinimides as halogen sources was described via C−H activation under mild reaction conditions. A series of halogen-substituted 2-arylquinazolines were synthesized through C−H functionalization. An efficient quinazoline-assisted ortho -halogenation of 2-arylquinazolines has been developed using N -halosuccinimides as halogen sources with Pd(II)-catalyzed C−H bond activation. No additional ligand and oxidant are required. This protocol is highly regioselective and applicable to a broad range of quinazoline substrates bearing different functional groups, giving yields of up to 98 %. The mechanism of the quinazoline ortho -halogenation was investigated by comprehensive experimentation.