An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1'-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO) and a bisquinolyldiamine ligand [(1,2)-,-di(quinolin-8-yl)cyclohexane-1,2-diamine, ]. A number of ligands (-) and the analogs of , with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.
View Article and Find Full Text PDFA copper-catalyzed annulation of alkyne-tethered enaminones for the synthesis of 2,3-ring fused pyrroles is reported. The 5--dig cyclization/olefin migration reaction delivers the multisubstituted pyrroles in 59-99% yields with 16 examples. This strategy features easily available starting materials, mild reaction conditions, and a cheap ligand-free copper catalyst.
View Article and Find Full Text PDFHerein we describe a general, mild and scalable method for deuterium incorporation by potassium methoxide/hexamethyldisilane-mediated dehalogenation of arylhalides. With CDCN as a deuterium source, a wide array of heteroarenes prevalent in pharmaceuticals and bearing diverse functional groups are labeled with excellent deuterium incorporation (>60 examples). The ipso-selectivity of this method provides precise access to libraries of deuterated indoles and quinolines.
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