Science of Synthesis

Hopkinson, M. N.; Gouverneur, V., Science of Synthesis Knowledge Updates, (2011) 2, 101.

General Introduction

Homo- and cross-coupling reactions catalyzed by transition metals are an increasingly important class of carbon–carbon and carbon–heteroatom bond-forming processes.[‌1‌] These transformations allow for the efficient coupling of diversely functionalized organic molecules with high selectivity and functional-group tolerance. As such, coupling reactions have become powerful tools for synthetic chemists with palladium-catalyzed processes, such as the Suzuki–Miyaura, Stille, and Sonogashira reactions, being the subject of the 2010 Nobel Prize in Chemistry.[‌2‌,‌3‌] Most coupling reactions proceed via a redox cycle where the metal catalyst Mn undergoes a two-electron oxidation to afford an Mn + 2 species amenable to reductive elimination. Whilst palladium is ideally suited to such cycles, other transition metals such as nickel and copper have emerged as alternative catalysts for homo- and cross-coupling reactions, expanding the range of transformations available to synthetic chemists.

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References