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Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated benzo[b]naphtho[2,1-d]thiophene Derivatives

Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated benzo[b]naphtho[2,1-d]thiophene Derivatives

Chin-Chau Chen, Chu-Mei Chen, Ming-Jung Wu

J Org Chem. 2014 May 16;79(10):4704-11.

PMID: 24750047

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP205436	Benzo[b]naphtho[1,2-d]thiophene		205-43-6	Price

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