Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated Benzo[b]naphtho[2,1-d]thiophene Derivatives
2014
Chen, Chin-Chau | Chen, Chu-Mei | Wu, Ming-Jung
Treatment of 2-(2-(2-(2-substituted ethynyl)phenyl)ethynyl)thioanisoles (1) with 5 mol % of Ph₃PAuCl/AgSbF₆ and 2 equiv of NIS at refluxing CH₂Cl₂ gave iodo-substituted benzo[b]naphtho[2,1-d]thiophene (6) in good yields. Chloro- and bromo-substituted benzo[b]naphtho[2,1-d]thiophene derivatives (8 and 9) were also generated by treating compound 1 with 5 mol % of PdX₂ and 3 equiv of CuX₂ at refluxing THF.
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