Copper-facilitated Suzuki-Miyaura coupling for the preparation of 1,3-dioxolane-protected 5-arylthiophene-2-carboxaldehydes

Tamás Hergert, Bálint Varga, Angelika Thurner, Ferenc Faigl, Béla Mátravölgyi

Research output: Contribution to journalArticle

Abstract

5-Formyl-2-thiopheneboronic acid is a widely used building block for the synthesis of diverse structures, however, due to a significant instability its transformation to 5-arylthiophene-2-carboxaldehydes by C–C couplings could be performed only in low yields. Herein, as a solution, a convenient technique is described for the preparation of 1,3-dioxolane-protected 5-arylthiophene-2-carboxaldehydes via a one-pot borylation–copper(I) chloride co-catalyzed Suzuki-Miyaura coupling reaction. The utilization of the in situ prepared 2-thiopheneboronic ester derivative is allowed by the method developed. Elimination of the crucial, acidic liberation step of boronic acid species resulted in improved yields and purities. In addition, comparison of various aryl bromides is shown to demonstrate the high tolerance of the transformation to functional groups.

Original languageEnglish
Pages (from-to)2002-2008
Number of pages7
JournalTetrahedron
Volume74
Issue number16
DOIs
Publication statusPublished - Apr 19 2018

Keywords

  • 5-Formyl-2-thiopheneboronic acid
  • Anchoring group precursor
  • Copper co-catalysis
  • Dye-sensitized solar cells
  • Suzuki-Miyaura coupling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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