Ruthenium-Catalyzed Carbon−Carbon Bond Formation via the Cleavage of an Unreactive Aryl Carbon−Nitrogen Bond in Aniline Derivatives with Organoboronates

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Abstract

The RuH2(CO)(PPh3)3-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon−nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon−nitrogen bond in anilines to the ruthenium complex, and (2) C−C bond formation takes place via transmetalation between the Ru−NR2 species and organoboronates.

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