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Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes.

The direct conversion of C H bonds into C C bonds leads to a more efficient synthesis with a reduced number of synthetic operations. Recently, progress has been made in the transition-metal-catalyzed activation and subsequent reaction of C H bonds. On the other hand, we and others have developed various methods to generate C C bonds directly from two different C H bonds in the presence of an oxidizing reagent through a cross-dehydrogenative-coupling (CDC), which is catalyzed by copper or other transition-metals. However, in all these cases, a relatively reactive C H bond (e.g. 1,3-dicarbonyls, alkynes, and nitroalkanes) is required. Recently, an elegant cross-coupling reaction of two aryl C H bonds to form arene–arene coupling products was reported by Fagnou and co-workers, and others. We have also reported a direct alkylation of 1,3-dicarbonyl compounds by using simple alkanes in the presence of a peroxide. Herein, we report an unprecedented direct oxidative cross-coupling of arenes with cycloalkanes catalyzed by ruthenium (Scheme 1).