Journal
SYNTHESIS-STUTTGART
Volume 54, Issue 3, Pages 732-740Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1719849
Keywords
Meerwein arylation; arenediazonium salts; 3-hydroxythiophenes; Fiesselmann reaction
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Methyl 3-aryl-2-bromo-2-chloropropanoates were prepared via Meerwein reaction catalyzed by copper(II) bromide, and were utilized as starting materials for the synthesis of substituted 3-hydroxythiophenes. The structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes was achieved due to the wide range of available starting materials, including both anilines and thiols.
Methyl 3-aryl-2-bromo-2-chloropropanoates can be prepared by Meerwein reaction from methyl 2-chloroacrylate and various arenediazonium salts under copper(II) bromide catalysis. The resulting readily available compounds were used as starting materials in reactions with substituted methanethiols for the construction of substituted 3-hydroxythiophenes which have not yet been accessible by other routes. Structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes has been achieved due to a wide range of available starting materials, including both anilines and thiols.
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