Palladium and Copper Catalyzed Sonogashira Decarboxylative Coupling of Aryl Halides and Alkynyl Carboxylic Acids

Yoan Chevalier (1) , Carine Maaliki (1) , Emilie Thiery (1) , Jérôme Thibonnet (1)

1 UMR ISP - Infectiologie et Santé Publique

The Sonogashira cross-coupling reaction is the most useful tool for the formation of the C(sp2) – C(sp) bond and it is used as a key step in total synthesis. This reaction proceeds via palladium catalyzed coupling between aryl halides and terminal alkynes in the presence of copper salts as co-catalysts. One limitation of this coupling is the alkyne source, in particular the use of volatile terminal alkynes. The decarboxylative Sonogashira reaction between aryl halides and alkynyl carboxylic acids has emerged as an alternative to the Sonogashira reaction, and terminal alkynes are replaced by the corresponding alkynyl carboxylic acids that are easily available and stable for handling and storage. A mild procedure of palladium and copper catalyzed decarboxylative cross-coupling reaction of aryl halides and alkynyl carboxylic acids has been developed. Low molecular weight acids, to introduce small building blocks, were specifically used. This methodology is easy to implement and uses common reactants and catalysts.

Domaines: Chimie; Chimie organique

Yoan Chevalier, Carine Maaliki, Emilie Thiery, Jérôme Thibonnet. Palladium and Copper Catalyzed Sonogashira Decarboxylative Coupling of Aryl Halides and Alkynyl Carboxylic Acids . Journées de Chimie Organique, Sep 2016, Palaiseau, France. 2016. ⟨hal-01822869⟩