Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation

(Chemical Equation Presented) The first observation of cleavage of unactivated aromatic C-N bonds on a late-transitionmetal center was achieved using o-acylanilines and a ruthenium complex. Use of olefins as additives dramatically improved the rate of C?N bond cleavage. The carbon fragment remaining on the ruthenium after C?N bond cleavage was coupled with a phenylboronate to form a biphenyl framework. The present results suggest that ruthenium-catalyzed C-C bond formation from o-acylaniline and organoboronate proceeds via direct C?N bond cleavage on the ruthenium center.