A practical synthesis of axially chiral biaryls via chirality transfer from peripheral stereogenic carbon centers is reported. In contrast to the traditional aromatization process of a non-aromatic structure with ipso stereogenic centers, this method is based on a Pd-catalyzed carbon-carbon bond cleavage/ring-opening reaction of optically active 8H-indenothiophen-8-ols with an achiral ligand, enabling synthesis of highly functionalized 3-arylthiophene atropisomers in high enantioselectivity.