Stable cyclopalladated complexes containing an (sp3)C-Pd bond were synthesized via α-CH2 deprotonation and palladation of N-alkyl groups of carbene ligands bearing electron-withdrawing substituents. The strong electron donating strengths of the resulting CNHC^Csp3 chelators were experimentally identified, and the palladacycle underwent template-directed, versatile C-halogenation with X2.