4.7 Article

Lewis acids as highly efficient catalysts for the decarboxylative esterification of carboxylic acids with dialkyl dicarbonates

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 345, Issue 8, Pages 943-947

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200303040

Keywords

carboxylic acids; catalysis; dialkyl dicarbonate; esterification; esters; Lewis acids

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Mild Lewis acids such as Mg(ClO4)(2) show a new level of catalytic activity for the decarboxylative esterification of carboxylic acids with commercially available dialkyl dicarbonates. In the presence of as little as one mol % Mg(ClO4)(2) catalyst, carboxylic acids can thus easily and near quantitatively be protected at room temperature, e.g., as methyl, benzyl, or t-butyl esters. Only volatile by-products are released so that the purification of the products is particularly easy. Many sensitive functionalities are tolerated, including even phenol esters, or free hydroxy and BOC groups.

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