Amine containing substrates are important building blocks for a variety of biological and pharmaceutical compounds. However, application of the otherwise versatile Suzuki reaction to these substrates has proved challenging due to either ligation of the amine to the palladium or to electronic effects slowing the oxidative addition step. Conventional methods to overcome these challenges involve protection-deprotection strategies or the use of designer ligands to facilitate reaction. We have shown that application of CO2 pressure and adjusting the water content of the reaction system facilitate the Suzuki coupling of 4-amino-2-halopyridines in high yield with the simple Pd(TPP)2Cl2 catalyst. The protocol was expanded to 2-halopyridines. The results of these investigations will be discussed.

Effect of pH in the development of high-yielding Suzuki coupling reactions of basic, amine containing substrates

248th National Meeting (2014)

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