The introduction of Nitrogen atoms into organic molecules is one of the most important transformations in organic chemistry.  While transition-metal catalyzed reactions for aryl-nitrogen bond formation have been well developed, analogous methods for the formation of alkyl-nitrogen bonds remains largely unexplored.  With the ultimate goal of developing such reactions, we have discovered conditions for the copper-catalyzed alkylation of primary amides using primary boronic acids. This C�N bond forming reaction allows for the selective mono-N-alkylation of primary amides, a reaction that is exceedingly challenging using traditional electrophilic alkylation techniques. The discovery of the reaction conditions, as well as the scope and limitations of the process will be described.

Copper-catalyzed mono-alkylation of primary amides using alkyl boronic acids

244th National Meeting (2012)

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