Reactions that forge carbon-carbon (C-C) bonds are the bedrock of organic synthesis, widely used across the chemical sciences. We report a transformation that enables C-C bonds to be constructed from two classes of commonly available starting materials, alkenes and carbon hydrogen (C-H) bonds. The reaction employs a palladium(II) catalyst and utilizes a removable directing group to both control the regioselectivity of carbopalladation and enable subsequent proto-depalladation. A wide range of alkenes and C-H nucleophiles, including 1,3-dicarbonyls, aryl carbonyls, and electron-rich aromatics, are viable reaction partners, allowing Michael-type reactivity to be expanded beyond alpha,beta-unsaturated carbonyl compounds to unactivated alkenes. Applications of this transformation in drug diversification and natural product total synthesis are described. Stoichiometric studies support each of the proposed steps in the catalytic cycle.