Palladium-Mediated Fluorination of Arylboronic Acids

Palladium-mediated fluorination of arylboronic acids.

Palladium(III)-catalyzed fluorination of arylboronic acid derivatives.

A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multigram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized.

Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids.

A highly efficient and mild palladium-catalyzed decarboxylative cross-coupling of aryl boronic acids and alkynyl carboxylic acids for the synthesis of unsymmetrical substituted alkynes is described for the first time.

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.