SuzukiMiyauraKupplungen

The Suzuki–Miyaura coupling, commonly referred to in German-language literature as Suzuki-Miyaura Kupplungen, is a palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides or pseudohalides. The reaction typically uses boronic acids or boronate esters as the organoboron partner and aryl or vinyl halides as the electrophile, producing biaryl, alkenyl, or aryl–alkenyl products.

It was developed independently by Akira Suzuki and Norio Miyaura and coworkers in the late 1970s and early 1980s. The method rapidly became one of the most versatile tools for constructing C–C bonds due to mild conditions and broad functional-group tolerance. Since its introduction, numerous refinements have expanded substrate scope and practical applicability.

Substrates include aryl, vinyl, and, with more specialized conditions, alkyl partners; organoboron reagents include boronic acids, boronate esters, and organotrifluoroborates. Electrophiles include aryl and vinyl halides, triflates, and related leaving groups. Commonly used bases are inorganic hydroxides or carbonates; reactions often run in mixed aqueous-organic solvents.

The catalytic cycle involves oxidative addition of the electrophile to Pd(0), transmetalation with the organoboron partner in the presence of base, and reductive elimination to form the new C–C bond and regenerate Pd(0). The base promotes transmetalation and helps stabilize boron species.

Palladium catalysts are typically paired with phosphine or newer biaryl ligands (eg, SPhos, XPhos, tBu3P). Ligand choice and reaction conditions are tuned to substrate class, with common solvents including dioxane, toluene, and water-containing mixtures, at ambient to moderate temperatures.

The Suzuki–Miyaura coupling is widely used in pharmaceuticals, agrochemicals, and materials science for constructing biaryl motifs and conjugated systems. Its robustness, ease of handling boron reagents, and compatibility with sensitive functional groups have made it a staple of modern organic synthesis.