title: 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.
abstract: 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 PhI(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.
authors.affiliation: Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA.
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.forename: Darrin M
authors.initials: DM
authors.lastname: Flanigan
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: Paul R
authors.initials: PR
authors.lastname: Blakemore