The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-伪-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the 伪-arylation of acetone with aryl halides.