Chemical Communications 2008-11-30

Rhodium(I)-catalyzed one-pot synthesis of dialkyl ketones from methanol and alkenes through directed sp3 C-H bond activation of N-methylamine.

Eun-Ae Jo, Ji-Hyun Lee, Chul-Ho Jun

Index: Chem. Commun. (Camb.) (44) , 5779-81, (2008)

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Abstract

The hydroacylation of methanol with alkenes was developed using a catalytic system consisting of Rh(I), 2-amino-4-picoline and benzoic acid; the reaction is speculated to occur by the initial N-methylation of 2-amino-4-picoline with methanol, and the subsequent dehydrogenation of the resulting N-methylamine, followed by double chelation-assisted hydroimination of alkene with the imine to give dialkyl ketones after hydrolysis.