Nickel-Catalyzed C-H Alkynylation of Anilines: Expedient Access to Functionalized Indoles and Purine Nucleobases

C-H alkynylations of electron-rich anilines were accomplished by means of user-friendly nickel catalysis. The C-H functionalization occurred with high positional selectivity and ample scope by kinetically relevant C-H activation. The robust nickel catalyst tolerated synthetically useful functional groups, which set the stage for the facile synthesis of substituted indoles. The chemoselectivity of the cost-effective nickel catalyst was reflected by enabling transformative nickel-catalyzed C-H functionalization with purine nucleobases through monodentate chelation assistance.