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New strategy for the synthesis of 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene derivatives


Pd-catalyzed coupling reactions like the Sonogashira coupling reaction are very useful tools for the formation of new carbon–carbon bonds under mild reaction conditions. Coupling reactions are also used for elaboration of organic compounds in drug and material discovery. Terminal alkynes have a very critical role in Sonogashira coupling reaction. Therefore, design and synthesis of new terminal alkynes are very important for the preparation of organic compounds. In the present study, a novel alkyne 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene 13 was synthesized, and it was tested for Sonogashira coupling reaction with different iodoaryl compounds. It was investigated whether our terminal alkyne 13 having a special construction might be a useful precursor for the synthesis of potentially active organic molecules.

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The authors thank The Scientific and Technological Research Council of Turkey (Project no: 115Z020) for providing financial support for obtaining reactant and reagents, and Van Yüzüncü Yil University (Project no: FBA-2017-6007) for providing financial support for obtaining solvents, glasswares and salts. We thank University of Duhok for the scholarship given to Muheb A.S. Algso. The authors would also like to acknowledge networking contribution by the COST Action CM1407.

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Correspondence to Arif Kivrak.

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Characterization of the new benzo[b]thiophene products including 1H NMR, 13C NMR, and FTIR spectra, as well as mass characterization data. (DOC 42003 kb)

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Algso, M.A.S., Kivrak, A. New strategy for the synthesis of 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene derivatives. Chem. Pap. 73, 977–985 (2019).

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  • Alkynes
  • Benzothiophenes
  • Sonogashira coupling reaction
  • C–C bond formation reactions