Icosahedral carborane anions such as CHB11Cl11- are amongst the least coordinating, most chemically inert anions known. They are also amongst the least basic, so their conjugate acids, H(carborane), are superacids (i.e. stronger than 100% H2SO4). Acidity scale measurements indicate that H(CHB11Cl11) is the strongest pure Brønsted acid presently known, surpassing triflic and fluorosulfuric acid....

Polymetalated aromatic compounds are particularly challenging synthetic goals because of the limited thermodynamic stability of polyanionic species arising from strong electrostatic repulsion between adjacent carbanionic sites. Here we describe a facile synthesis of two polyaurated complexes including a tetra-aurated indole and an octa-aurated benzodipyrrole. The imido trinuclear gold(I) moiety...

A novel type of deprotonative functionalization of aromatics was accomplished with a phosphazene base (t-Bu-P4 base). For various nitrogen heteroaromatics and benzene derivatives, deprotonative 1,2-additions proceeded with the t-Bu-P4 base and ZnI(2) as an additive in the presence of carbonyl compounds. The t-Bu-P4 base has both extremely strong Brønsted basicity and less nucleophilicity due to...

Specific rates of solvolysis in hydroxylic solvents available for the solvolysis of 2-thiophenesulfonyl chloride and phenylmethanesulfonyl chloride are supplemented by determining the values in fluoroalcohol-containing solvents. The data sets are then correlated using the extended Grunwald-Winstein equation. For both substrates, it is found that a single correlation controls the influence of so...

Theoretical calculations were carried out to understand the effect of annulation on the electronic and ligand properties of boron substituted N-heterocyclic carbenes (B-NHCs). Annulation results in a decrease in stability as indicated by the calculated values of singlet-triplet separations and stabilization energies as well as HOMO-LUMO gaps. Annulated B-NHCs are found to be weaker σ-donors but...

The glycosylation reaction is the key transformation in oligosaccharide synthesis, but it is still difficult to control in many cases. Stereocontrol during cis-glycosidic linkage formation relies almost exclusively on tuning the glycosylating agent or the reaction conditions. Herein, we use nucleophile-directed stereocontrol to manipulate the stereoselectivity of glycosylation reactions. Placin...

There is a renewed interest in designing solid acid catalysts particularly due to the significance of Lewis acid catalyzed processes such as Friedel-Crafts acylation and alkylation and cellulose hydrolysis for the development of sustainable chemistry. This paper reports a new focus point on the properties of supported CuO on silica, a material that up to now has been considered only as the prec...

In this paper, the synthesis of different bisglucosides is investigated through reaction two acetylated glucose units with a diol (or diphenol) in order to develop versatile molecular platform for future development bio-based polymers. A panel five diols and one diphenol initially used examine influence their chemical skeleton on yield both nature proportion formed species. Reaction products ar...

The reaction of 5-hydroxymethylfurfural (5-HMF) with arenes in superacidic trifluoromethanesulfonic acid (triflic acid, TfOH) as the solvent at room temperature for 1-24 h gives rise to 5-arylmethylfurfurals (yields of 17-91%) and 2-arylmethyl-5-(diarylmethyl)furans (yields of 10-37%). The formation of these two types of reaction products depends on the nucleophilicity of the arene. The same re...