Hartwig Nickel Precatalysts

Introduction

Suzuki-Miyuara couplings have been widely commonplace in the formation of C-C bonds, in particular the coupling between two heteroaryl compounds. For the most part, palladium has been the dominant choice of metal catalyst to carrying out cross-coupling reactions between heteroaryl boronic acids and heteroaryl halides. Nickel catalysts also possess the ability to mediate Suzuki-Miyuara couplings, however have been less often reported mainly due to lack of scope and high catalyst loadings. Sigma-Aldrich now provides two new single-component, Ni-catalysts (L511706 and L511714) which effectively catalyze the formation of heteroaryls from a wide scope of various N, O and S containing boronic acids and heteroaryl halides.

Advantages

Unlike most Nickel and Palladium sources, Ni-catalysts L511706 and L511714 both are stable to both air and moisture. These catalysts possess high catalytic activity (less than 1 mol %) without any added ligand and are not poisoned by the presence of N, O or S. Possibly the most important problem these single-component complexes solve, is the issue with protodeborylation that occurs from Suzuki-Miyuara couplings of heteroaryl boronic acids. A minimal amount of protodeborylation is observed in a wide range of examples shown in the report by Hartwig and coworkers.1

Representative Applications

Materials

     

To learn more about other products in our catalog that have been established in collaboration with Professor Hartwig, please visit his Professor Product Page.

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