A facile two-step synthesis of thiophene end-capped aromatic systems

作者：Rungtaweevoranit Bunyarat; Butsuri Akkarapol; Wongma Krittaphat; Sadorn Karoon; Neranon Kitjanit; Nerungsi Chakkrapan; Thongpanchang Tienthong^*

来源：Tetrahedron Letters, 2012, 53(14): 1816-1818.

DOI：10.1016/j.tetlet.2012.01.122

• Naphthodithiophene
• Nucleophilic aromatic substitution
• Oxygen-sulfur replacement
• Sulfur-containing aromatic heterocycles
• Thiophene

Thiophene end-capped aromatic analogues, that is, naphthothiophenes, naphthodithiophenes, pyrenothiophene, and benzotrithiophene, can be prepared from commercially available hydroxyarenes in two steps, including (1) a consecutive acid-mediated nucleophilic aromatic substitution of hydroxyarenes with 2-mercaptoethanol, followed by cyclization to form an arene-fused dihydrothiophene, and (2) oxidation of the dihydrothiophene unit to thiophene.

• 出版日期2012-4-4