α-Amino acids are abundant feedstock chemicals for organic synthesis. Numerous methods have been developed to transform these useful starting materials into a number of valuable products. However, strategies for functionalization via cleavage of the carbon-nitrogen (C-N) bond remain limited. We have recently developed a nickel-catalyzed cross coupling of alkylpyridinium salts and aryl boronic acids. We have now developed a nickel-catalyzed Suzuki-Miyaura cross coupling of pyridinium salts derived from α-amino acids. When coupled with an efficient synthesis of the pyridinium salt in a single step from the amino ester, this method provides easy access to α-arylated carboxylic acids and esters from readily available α-amino acids. The optimization, scope, and mechanistic understanding of these reactions will be presented.

Transforming α-amino acids to α-aryl acids via nickel-catalyzed C–N bond activation

254th National Meeting (2017)

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