Nucleophilic addition of N-benzylsulfonamides to 1-bromo-1-alkynes proceeded in a highly regio- and stereoselective manner to give (Z)-N-benzyl-N-(1-bromo-1-alken-2-yl)sulfonamides. These adducts cyclized via Pd-catalyzed aromatic C-H bond activation to afford 1,2-dihydroisoquinolines in good yields.