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The HSAB principle in designing Bis(imino)acenaphthene N‐heterocyclic carbene (NHC) palladium complexes is presented. N‐donor ligands serve as hard bases to enhance the catalytic activities of NHC Pd complexes in Suzuki and Buchwald–Hartwig amination reactions. The Pd complex bearing tertiary amine ligands exhibited higher performance in coupling reactions than those exhibited by other soft base ligands reported in literature. 48 coupling products were generated in moderate‐to‐complete yields in the presence of aryl chlorides as substrates for Suzuki and amination reactions in air under mild conditions. [ABSTRACT FROM AUTHOR]