Volume 32, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Substituted Alkyne Synthesis under Nonbasic Conditions: Copper Carboxylate-Mediated, Palladium-Catalyzed Thioalkyne—Boronic Acid Cross-Coupling.

Cecile Savarin

Cecile Savarin

Dep. Chem., Emory Univ., Atlanta, GA 30322, USA

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Jiri Srogl

Jiri Srogl

Dep. Chem., Emory Univ., Atlanta, GA 30322, USA

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Lanny S. Liebeskind

Lanny S. Liebeskind

Dep. Chem., Emory Univ., Atlanta, GA 30322, USA

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First published: 27 May 2010

Abstract

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ChemInform Abstract

A novel mild and efficient synthesis of internal alkynes (III) is presented, involving the palladium-catalyzed, copper carboxylate-promoted cross-coupling of thioalkynes (I) with boronic acids (II). The method tolerates a wide range of alkenyl, hetaryl, and aryl substituents (containing electron-donating or electron-withdrawing groups) at both the thioalkynes and the boronic acids.

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