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Synfacts 2022; 18(08): 0891
DOI: 10.1055/s-0041-1738243
Metals in Synthesis

The Liebeskind–Srogl Cross-Coupling

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
Liebeskind LS, *, Srogl J. * Emory University, Atlanta, USA
Thiol Ester–Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone Synthesis.

J. Am. Chem. Soc. 2000;
122: 11260-11261
DOI: 10.1021/ja005613q
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Key words

boronic acids - copper - cross-coupling - ketones - palladium catalysis - thioesters

Significance

In 2000, Liebeskind and Srogl disclosed a copper(I)-promoted palladium-catalyzed cross-coupling of thioesters and boronic acids for the synthesis of ketones under neutral conditions. This base-free desulfitative process is mediated by a palladium(0) catalyst and stoichiometric amounts of a copper(I) carboxylate salt.


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Comment

The copper(I) carboxylate CuTC is a key feature of this transformation as it facilitates both the C(sp2)–S bond cleavage via coordination of the copper center by the sulfur atom and the activation of the boronic acid through coordination of the carboxylate unit to the boron atom. Since its discovery, the Liebeskind–Srogl coupling has been thoroughly studied, and the scope of this transformation has been considerably extended.


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Review

H. Prokopcová, C. O. Kappe Angew. Chem. Int. Ed. 2009, 48, 2276–2286.


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Publication History

Article published online:
18 July 2022

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