Nitroalkanes are commonly used building blocks in organic synthesis. Although these molecules are competent nucleophiles in a wide range of reactions, the C-alkylation of nitroalkanes with simple alkyl electrophiles remains a significant challenge. The difficulty stems from the inherent preference for nitronate anions to undergo O-alkylation under simple base-promoted reaction conditions. Recent efforts in our lab have led to the discovery of reaction conditions to overcome this long-standing problem. We have found that the use of transition-metal based catalysts results in the C-alkylation of nitroalkanes using simple alkyl halide electrophiles. This method allows for the rapid synthesis of complex nitroalkanes by the direct alkylation of simple nitroalkane starting materials. The development, scope and limitations of the method, as well as its application to the synthesis of complex amines, will be discussed.

Transition-metal catalyzed C-alkylation of nitroalkanes

243rd National Meeting (2012)

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