Preparation and catalytic applications of partially fluorinated binaphthol ligands

Aerobic Copper-Catalyzed Organic Reactions

“…This method proved less cumbersome than the Ullmann coupling for the synthesis of partially fluorinated systems. 662 …”

“…662 While the chemoselectivity was low, these conditions were still an improvement over the Ullmann coupling.…”

Aromatic Fluorine as a Versatile Control Element for the Construction of Molecules with Helical Chirality

“…Encouraged by these findings, we pursued cyclization precursors with “mixed” electronic characteristics as we supposed that such donor/acceptor systems could exhibit modulated interactions in the solid state 15. Importantly, there was also the possibility of being able to compare such species with 6 directly due to the very similar steric requirements of H and F. Indeed, we were able to synthesize the helically chiral compound 8 by refluxing the F 4 ‐binol13b precursor 7 as a template with KOH in THF (Scheme ). Attempts to isolate enantiopure 8 proved unsuccessful as the compound readily racemizes at room temperature.…”

Aryloxy tetrazoles with axial chirality: Synthesis and partial resolution of 5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole

“…Optically active BINOL and its relative compounds with axial chirality have wide application in asymmetric ligands [5,6], Michael addition [7], enantioselective hydrogenation [8], and chiral-reducing agents [9,10] and more [11][12][13][14].…”