Organic & biomolecular chemistry

Palladium-catalysed synthesis of aryl-alkyl ethers using alkoxysilanes as nucleophiles

EJ Milton, JA Fuentes, ML Clarke

Index: Milton, Edward J.; Fuentes, Jose A.; Clarke, Matthew L. Organic and Biomolecular Chemistry, 2009 , vol. 7, # 12 p. 2645 - 2648

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Citation Number: 25

Abstract

Changing the activator from tetrabutyl ammonium fluoride (TBAF) to sodium hydroxide unexpectedly switches the catalytic pathway of the Hiyama coupling reaction of vinyl trialkoxysilanes with aryl bromides into a Pd catalysed C–O bond forming reaction; if the correct conditions are used, high yields of aryl-alkyl ethers are observed. In addition, coupling between readily available tetraalkoxysilanes and aryl bromides can also be ...

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