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Bromoarylation of Methyl 2-Chloroacrylate under Meerwein Conditions for the Synthesis of Substituted 3-Hydroxythiophenes

Yurii V. Ostapiuk*, Maksym Shehedyn, Oksana V. Barabash, Bohdan Demydchuk, Sviatoslav Batsyts, Colin Herzberger, Andreas Schmidt*

*Ivan Franko National University of Lviv, 79005 Lviv, Ukraine; Clausthal University of Technology, 38678 Clausthal-Zellerfeld, Germany, Email: yurii.ostapiuklnu.edu.ua, schmidtioc.tu-clausthal.de

Y. V. Ostapiuk, M. Shehedyn, O. V. Barabash, B. Demydchuk, S. Batsyts, C. Herzberger, A. Schmidt, Synthesis, 2022, 54, 732-740.

DOI: 10.1055/s-0040-1719849


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Abstract

Methyl 3-aryl-2-bromo-2-chloropropanoates, which can be prepared by Meerwein reaction from methyl 2-chloroacrylate and various arenediazonium salts under copper(II) bromide catalysis, were used as starting materials in reactions with substituted methanethiols for the construction of a broad range of substituted 3-hydroxythiophenes.

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Key Words

Meerwein arylation, arenediazonium salts, thiophenes, 3-hydroxythiophenes, Fiesselmann reaction


ID: J66-Y2022