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Liebeskind-Srögl Cross-Coupling

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr394

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Liebeskind-Srögl Cross-Coupling. Comprehensive Organic Name Reactions and Reagents. 394:1754–1757.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

It is a palladium-catalyzed coupling reaction between an aryl boronic acid and a general sulfur containing molecules to form a variety of compounds, including ketones, thioethers, etc and is known as the Liebeskind–Srögl cross coupling or Liebeskind–Srögl thiol ester-boronic acid cross-coupling. Various reaction conditions as well as catalysts have been discussed, which facilitate the reaction. Among the tested palladium catalysts is the most efficient catalyst for this coupling reaction. Study finds that the stoichiometric amount of copper(I) thiophene-2-carboxylate (CuTC) and Cu(I) carboxylate together with palladium catalyst help the coupling conditions. The solvent is also considered to be very crucial for the coupling. Several solvents have been recommended for the coupling, such as amide-based solvents, dioxane and THF, etc. It has been reported that thiourea can similarly couple with aryl boronic acid with the help of microwave irradiation. This reaction, like other coupling methods has wide application in organic synthesis.

Keywords:

  • copper(I) thiophene-2-carboxylate (CuTC);
  • Cu(I) carboxylate;
  • sodium iodide;
  • phenyl ketones