Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives

We developed two new catalytic transformations of anilines via oxidative addition of C–N bonds to ruthenium centers. One is ruthenium-catalyzed reductive deaminatoindeamination of N-alkylated o-acylanilines. The other one is catalytic coupling of N-alkylated o-acylanilines with olefins giving ortho-alkylated aromatic ketones via C–N bond cleavage. This reaction involves a ruthenium hydride species as an intermediate, formed after β-hydride elimination from the ruthenium amide species.