A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. Wi...

3-Nitroindoles behave as electron-poor aromatic compounds and react toward a number electron-rich species. This feature article presents an overview of this reactivity, mainly in (formal) dearomatizing cycloaddition reactions.

Glycals 1 and 2 react with methoxybenzene in the presence of SnCLj forming ^-substituted C-glycosyl compounds 4 and 5 + 6 respectively. Under similar conditions l -Obenzoylor methyl pent-2-enopyranos-4-uloses (7) and (8) react with electron rich aromatic compounds furnishing either C-glycosyl compounds or C-2 aryl substituted products depending on the nature of the aromatic component as well as...

Current models describe aromatic rings as polar groups based on the fact that benzene and hexafluorobenzene are known to have large and permanent quadrupole moments. This report describes a quantitative study of the interactions between oxygen lone pair and aromatic rings. We found that even electron-rich aromatic rings and oxygen lone pairs exhibit attractive interactions. Free energies of int...

The aza-Friedel–Crafts (aza-FC) reaction is a very powerful tool for forming C–C and C–N bonds, based on an acid-catalyzed addition of electron-rich aromatic compounds to imines.

[structure: see text] We report the synthesis and characterization of partially fluorinated condensed tetracyclic aromatic compounds. Typical edge-to-face/herringbone packing of nonfluorinated analogues is replaced here by columnar stacks with disk planes orthogonal to the columnar axes. Enhanced pi-overlap results with overlaid electron-poor and -rich regions.

Aromatic rings exhibit defined interactions via the unique aromatic π face. Aromatic amino acids interact favorably with proline residues via both the hydrophobic effect and aromatic-proline interactions, C-H/π interactions between the aromatic π face and proline ring C-H bonds. The canonical aromatic amino acids Trp, Tyr, and Phe strongly disfavor a polyproline helix (PPII) when they are prese...

We present a trifunctional scaffold designed for the solid-phase synthesis of trimodal compounds. This scaffold holds two alkyne arms in a free and TIPS-protected form for consecutive CuAAC (copper(I)-catalyzed azide-alkyne cycloaddition), one Fmoc-protected hydrazide arm for reaction with aldehydes, and one carboxylic acid arm with CF₂ groups for attachment to the resin and (19)F-NMR quantific...