Direct entry to optically pure 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) derivatives by an iron-catalyzed stereoselective oxidative cross-coupling reaction between 2-naphthol and 2-aminonaphthalene with a labile chiral auxiliary is reported. This efficient method offers entry to tailor-designed ( R )- and ( S)-NOBINs that are not accessible by any other means.
A selectivity-driven
catalyst design approach was adopted to address
chemoselectivity issues in the oxidative coupling of phenols. This
approach was utilized for developing a Co(II)[salen]-catalyzed aerobic
oxidative cross-coupling of phenols in a recyclable 1,1,1,3,3,3-hexafluoropropan-2-ol
(HFIP) solvent. The waste-free conditions offer a sustainable entry
to nonsymmetric biphenols via a mechanistic scheme that involves coupling
of a liberated phenoxyl radical with a ligated 2-naphthoxyl radical.
The copper(II) trifluoromethanesulfonate-catalyzed Pummerer reaction of β-ketosulfoxides with 1,3-dicarbonyl compounds or π-nucleophiles such as phenols, arenes, and tetraallylsilane is reported. The mild conditions provide an efficient entry to a novel class of polysubstituted 3-alkylthiofuran and polysubstituted 3-thiobenzofuran heterocycles from readily available materials.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.