Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes

Palladium-mediated fluorination of arylboronic acids.

Silver-mediated trifluoromethoxylation of aryl stannanes and arylboronic acids.

A silver-mediated cross-coupling of trifluoromethoxide with aryl stannanes and arylboronic acids to give aryl trifluoromethyl ethers is reported. This is the first report of a transition-metal-mediated C(aryl)-OCF(3) bond formation.

Highly effective copper-mediated gem-difluoromethylenation of arylboronic acids.

A copper-mediated gem-difluoromethylenation of aryl, heteroaryl and vinyl boronic acids with bromodifluoromethylated oxazole or thiazole derivatives has been developed. This novel reaction showed an excellent functional group tolerance and wide substrate scope, providing facile access to practical application in drug discovery and development.

Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts.

The ligand-free trifluoromethylation of arylboronic acids with a [Ph(2)SCF(3)](+)[OTf](-)/Cu(0) system has been carefully investigated. Aryl-, alkenyl- and heteroarylboronic acids with a variety of functional groups were suitable substrates for this reaction. It is suggested that a CuCF(3) species is formed under the reaction conditions.

Inhibition of serine proteases by arylboronic acids.

Arylboronic acids were found to be strong competitive inhibitors of subtilisin and chymotrypsin. The binding constants are strongly pH dependent and give a Hammett-type plot with a slope of -0.885. The pH dependence, the Hammett plot, and nmr model-system studies indicate that inhibition is due to electron-pair donation by the active site histidine to the bound inhibitor.