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Synthesis of 3-Acylbenzo[b]thiophenes via Mercury (II)-Catalyzed Cyclization reactionLin, Cheng-Han 20 July 2011 (has links)
Treatment of 1-(methylsulfinyl)-2-(phenylethynyl)benzene with 10 mol % of mercury dichloride and 1 equivalent of
2,3-dichloro-5,6-dicyano-1,4-benzoquinone in refluxing benzene gave benzo[b]thiophene in good yields. This method tolerated various functional
groups in phenylethynyl moiety, including electron donating groups and electron withdrawing groups. Useing
1-(benzylsulfinyl)-2-(phenylethynyl)benzene as reaction substrate increased the yields of benzo[b]thiophene derivatives. Isotope effect showed that this cyclization reaction belong to Pummerer type cyclization
reaction.
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