Abstract
(4-Chlorophenyl)-(1-oxo-1λ 4-benzo[b]thien-2-yl)methanone 2a was synthesized by oxidation of the corresponding benzo[b]thiophene derivative 2 with the oxidative system H 2O 2 TFA . This benzo[b]thiophene sulfoxide undergoes Michael-type nucleophilic addition of sulfur- and oxygen-containing nucleophiles either under basic conditions leading to 2,3-dihydro-3-substituted-benzo[b]-thiophene 1-oxides or in acidic media leading then to rearomatized 3-substituted-benzo[b]thiophenes. This method provides an easy two-step functionalization of 2-acyl-benzo[b]thiophene derivatives.
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