Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-Catalyzed Directed Double C-H Functionalization of 8,8′-Biquinolyl: Emergence of an Atropos from a Tropos State

7,7'-Dihydroxy-8,8'-biquinolyl(azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8'-biquinolyl mediated by Phl(OAc)(2), and (4) saponification. During the third step, an axially chiral (atropos type) biaryl molecule was directly generated from an essentially achiral (tropos type) biaryl starting material.