We report a site- and regioselective Heck-type arylation reaction for the synthesis of highly substituted 1,2-dihydropyridines from simple pyridine precursors. This transformation serves as a key step in our previously developed stepwise dearomative multi-functionalization platform, enabling the syn-addition of aryl halides to dihydropyridine intermediates under mild conditions. Comprehensive scope studies demonstrate broad functional group tolerance, accommodating both electron-rich and electron-deficient aryl iodides, a variety of N-protecting groups, and diverse C2 substituents