A one-pot method for the preparation of 2,5-diarylthiophene-1-oxides from arylacetylenes

TETRAHEDRON LETTERS

卷:57

Article

Miller, Robert W.¹  Dodge, Nicholas J.¹  Dyer, Adam M.¹  Fortner-Buczala, Eleanor M.²  Whalley, Adam C.¹ 

[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA

[2] Univ Vermont, Dept Microbiol & Mol Genet, Burlington, VT 05405 USA

关键词: Thiophene oxides;    Aryl acetylenes;    Zirconocene;    Metallole heterocycles;    Diels-Alder;   

DOI  :  10.1016/j.tetlet.2016.03.051

来源: Elsevier

【 摘 要 】

2,5-Diarylthiophene-1-oxides have been prepared from readily available arylacetylene precursors via zirconacyclopentadiene intermediates. The isolated yields of the desired thiophene-1-oxides are comparable to those obtained from the oxidation of thiophene derivatives while avoiding the formation of over-oxidation products. Furthermore, this route offers broader versatility than commonly used methods by providing products outfitted with electron-donating or electron-withdrawing groups with very little variation in isolated product yields. Finally, this strategy provides access to products containing functional groups that are not compatible with oxidation conditions. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

Free