Browsing by Author "Lackner, Sebastian"

The C-H alkylation of aniline derivatives with both primary and secondary alkyl halides was achieved with a versatile nickel catalyst of a vicinal diamine ligand. Step-economic access to functionalized 2-pyrimidyl anilines, key structural motifs in anticancer drugs, is thus provided. The C-H functionalization proceeded through facile C-H activation and SET-type C-X bond cleavage with the assistance of a monodentate directing group, which could be removed in a traceless fashion.

A versatile nickel catalyst allowed for C-H alkylations of unactivated arenes with challenging secondary alkyl bromides and chlorides. The high catalytic efficacy also set the stage for direct secondary alkylations of indoles as well as C-H trifluoroethylations with ample substrate scope.

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.