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Mild Decarboxylative Activation of Malonic Acid Derivatives by 1,1'-Carbonyldiimidazole

Danny Lafrance*, Paul Bowles, Kyle Leeman and Robert Rafka

*Development Science and Technology, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, United States, Email: Danny.lafrancepfizer.com

D. Lafrance, P. Bowles, K. Leeman, R. Rafka, Org. Lett., 2011, 13, 2322-2325.

DOI: 10.1021/ol200575c (free Supporting Information)


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Abstract

Malonic acid derivatives undergo unusually mild decarboxylation in the presence of N,N′-carbonyldiimidazole (CDI) at room temperature to generate a carbonyl imidazole intermediate in high yield. Subsequent reactions with various nucleophiles in an efficient one-pot process leads to amides, esters or carboxylic acids.

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Key Words

decarboxylation, amides


ID: J54-Y2011-1320