Owing to the prevalence of amino acids as key units in medicinal chemistry and important building blocks in organic synthesis, the development of synthetic useful methods to afford a variety of non-natural amino acid is of central importance in virtually every related bio- organic area. Direct functionalization of amino acids via C-H activation is an attractive strategy to accomplish this important goal.The seminar will describe an efficient methodology for PdII-catalyzed arylation of ? C(sp3)-H bonds of amino acids bearing a N-heteroarysulfonyl group with aryl iodides. The reactions tolerate a wide range of amino acids and aryl iodides. Furthermore, under the optimal reaction conditions no racemisation of the arylated amino acids were detected. In addition, these results prove the ability of the N-(2-pyridyl)sulfonyl group to activate C(sp3)-H bonds and represent a significant advance in the field of functionalization of unactivated C(sp3)-H bonds.

Palladium-catalyzed γ-arylation of of amino acids via direct C-H activation

244th National Meeting (2012)

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