Facile syntheses of homoleptic diarylmercurials via arylboronic acids

A general procedure for the syntheses of diarylmercurials is presented. Reactions proceeded in isopropanol in the presence of a base and arylboronic acid. With one exception, all reactions proceeded in good to excellent yields, and this procedure was applicable to a variety of aromatic and heteroaromatic boronic acids. Products were characterized by multinuclear NMR spectroscopy and microanalysis, and investigated by DFT calculations. The structure of di(4-pyridyl)mercury (6) was further authenticated by X-ray crystallography. Combined with previous work on the formation of arylgold(I) complexes via arylboronic acids, this procedure may be generally useful for the arylation of late transition metals.

Graphical abstractMercury–carbon bond formation between mercury(II) acetate and arylboronic acids in the presence of cesium carbonate occurs in moderate to excellent yields. A variety of functional groups and steric bulk are tolerated on the arylboronic acid.Figure optionsDownload full-size imageDownload as PowerPoint slide