Decarboxylation reactions are used in chemistry to synthesize or create molecules, and in recent years, transition metals have been used as catalysts to enable decarboxylative coupling reactions. These reactions are of interest because they increase the complexity of molecules in a single step. These reactions typically require an organometallic reagent, such as palladium, and are effective in forming C-C bonds. These metal-catalyzed decarboxylations typically require anion-stabilizing groups, adjacent to the decarboxylated ester. During the course of our synthesis of clinprost, we recently discovered a decarboxylation reaction of a pentadienyl dienoate that did not require an anion stabilizing group (see graphic). To better understand this novel decarboxylative coupling reaction, a series of substrates have been synthesized and studied. The mechanistic information obtained will be utilized to design additional new reactions.

Palladium catalyzed decarboxylation reactions of nonsymmetrical pentadienyl dienoates

248th National Meeting (2014)

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