Abstract

Furan-2-ylmethyl, thien-2-ylmethyl and pyrrol-2-ylmethyl tosylacetates undergo facile decarboxylative Claisen rearrangement upon exposure to N,O-bis(trimethylsilyl)acetamide-potassium acetate to yield the corresponding 2,3-disubstituted heteroaromatic products in good yield. However, for 1-(thien-2-yl)ethyl tosylacetates and substrates derived from 3-(hydroxyalkyl)indoles rearomatisation does not occur.

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