Reaction of bis(bis(trimethylsilyl)amido)mercury(II) with 3,3′-disubstituted binaphthols: Cyclization via an intramolecular electrophilic aromatic substitution reaction

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…The Cu(I)-mediated cyclization methodology shown here is an alternative to the earlier approach using a Hg(II) oxidant. 270 Photophysical and electrochemical data showed that the extension of the 134.4 PXX core into the molecular ribbon 134.7 reduced the band gap. This change was caused by an increase of the HOMO energy from −5.14 eV in 134.4 to −4.74 eV in 134.7 , which is a desirable feature for prospective p-type organic semiconductors.…”

O-Annulation Leading to Five-, Six-, and Seven-Membered Cyclic Diaryl Ethers Involving C–H Cleavage

“…In 2007, Weinert and co-workers studied the oxidation of 3,3′-disubstituted BINOL in the presence of a sterically encumbered mercury salt, (Hg[N(SiMe 3 )] 2 ) (50). 47 Depending on the equivalent of oxidant involved in the reaction, they were able to isolate monopyranyl pentacyclic 54. Based on 1 H and 199 Hg NMR, they have proposed a mechanistic pathway involving a mercuration reaction of the hydroxyl groups followed by intramolecular electrophilic aromatic substitution and extrusion of elemental Hg (Scheme 15).…”

“…Similarly, Fuchs and co-workers used on-surface protocols to produce DBF-and/or PXX-polymers from 6,6′-dibromo-BINOL derivatives. 37 Scheme 15 Proposed formation mechanism for PXX by Weinert and co-workers 47 Building on the Cu-based protocols, our group could achieve the synthesis of extended PXX derivatives. In particular, O-doped armchair 56, 57 49 and zig-zag 58 52…”

Dispersion Makes a Difference – The Solid‐State Structure of Hg[N(SiMe3)2]2

“…It was synthesized by a metathesis reaction of NaN(SiMe 3 ) 2 with HgBr 2 (Scheme ). Since then, compound 1 has found widespread use, for example, as a starting material for the synthesis of mercury–chalcogene compounds,, earth alkali silyl amides, organomercury compounds, in transition metal complexes and cyclisation reactions …”