Nucleophilic Acylation of o-Quinone Methides: An Umpolung Strategy for the Synthesis of α-Aryl Ketones and Benzofurans
Journal of the American Chemical Society2007Vol. 129(15), pp. 4508–4509
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Abstract
The synthesis of α-aryl ketones is accomplished by the direct nucleophilic acylation of o-quinone methide electrophiles. In this process, two reactive intermediates, carbonyl anions and o-quinone methides, are generated in one flask upon treatment of the corresponding thiazolium carbinols and silyl protected phenols with a soluble fluoride source. These intermediates then undergo productive addition reactions to afford the desired α-aryl ketone adducts. This new strategy has been applied to a short synthesis of the natural product demethylmoracin I.
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