Rhodium-Catalyzed Arylation Using Arylboron Compounds: Efficient Coupling with Aryl Halides and Unexpected Multiple Arylation of Benzonitrile

[reaction: see text]. The Suzuki-Miyaura-type cross-coupling of arylboron compounds with aryl halides proceeds efficiently in the presence of a rhodium-based catalyst system to produce the corresponding biaryls. Furthermore, it has unexpectedly been observed that the treatment with benzonitrile under similar conditions brings about its multiple arylation, in which nucleophilic arylation on the cyano group and subsequent ortho arylation via C-H bond cleavage are involved.