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

Autor:	Chao Wang, Paul R. Blakemore, Darrin M. Flanigan, Lev N. Zakharov
Rok vydání:	2011
Předmět:	Skraup reaction Stereochemistry Chemistry Organic Chemistry Molecule Surface modification Physical and Theoretical Chemistry Biochemistry Saponification Catalysis
Zdroj:	Organic letters. 13(15)
ISSN:	1523-7052
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::42cf601e55c845c206e37a397b92e8e6 https://pubmed.ncbi.nlm.nih.gov/21714530 Zobrazit plný text záznamu