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Regioselective Metal- and Reagent-Free Arylation of Benzothiophenes by Dehydrogenative Electrosynthesis.

Sebastian LipsDieter SchollmeyerRobert FrankeSiegfried R Waldvogel
Published in: Angewandte Chemie (International ed. in English) (2018)
A novel strategy for the synthesis of biaryls consisting of a benzothiophene and a phenol moiety is reported. These heterobiaryls are of utmost interest for pharmaceutical, biological, and high-performance optoelectronic applications. The metal- and reagent-free, electrosynthetic, and highly efficient method enables the generation of 2- and 3-(hydroxyphenyl)benzo[b]thiophenes in a regioselective fashion. The described one-step synthesis is easy to conduct, scalable, and inherently safe. The products are afforded in high yields of up to 88 % and with exquisite selectivity. The reaction also features a broad scope and tolerates a large variety of functional groups.
Keyphrases
  • highly efficient