Rhodium-catalyzed regioselective arylation of phenylazoles and related compounds with arylboron reagents via C–H bond cleavage

The rhodium-catalyzed direct ortho-arylation reactions of phenylazoles using arylboron reagents such as tetraarylborates were examined. Ethyl chloroacetate and potassium fluoride were found to effectively act as a hydrogen acceptor and a promoter, respectively, to afford selective formation of the corresponding mono- or diarylated products with good yields. In addition, azobenzene as well as 2-phenylpyridine also underwent the direct arylation under similar conditions.

Direct ortho-arylation of phenylazoles with arylboron reagents under rhodium catalysis proceeds efficiently to afford the corresponding mono- or diarylated products. Ethyl chloroacetate and potassium fluoride effectively act as a hydrogen acceptor and a promoter, respectively. Azobenzene as well as 2-phenylpyridine also undergo the direct arylation under similar conditions.Figure optionsDownload as PowerPoint slide