Palladium-catalyzed chemoselective decarboxylative cross coupling of benzoic acids with 伪-oxocarboxylic acids was realized via an arene sp2 C鈥揌 functionalization process. This work represents the first example of transition-metal-catalyzed cross-coupling reactions with two acids acting in different roles. The synthetic utility of this method was confirmed by the synthesis of pitofenone, an antispasmodic used in the combined drug Spasmalgon.