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Also known as: Suzuki Coupling, Suzuki Reaction
Discovered by Akira Suzuki (1979)
Palladium-catalyzed cross-coupling of an organoboron compound with an aryl halide. The most widely used cross-coupling reaction due to mild conditions, tolerance of many functional groups, and stability of boronic acids. Nobel Prize 2010.
Oxidative addition: Pd(0) inserts into the Ar-X bond to form Ar-Pd(II)-X.
Pd goes from 0 to +2 oxidation state
Transmetalation: Base activates the boronic acid (forming -ate complex). The Ar' group transfers from B to Pd, replacing X.
Base is essential — activates the boronic acid
Reductive elimination: The two aryl groups on Pd couple together, forming the Ar-Ar' product and regenerating Pd(0) catalyst.
Pd returns to 0 oxidation state — catalytic cycle complete
4-Bromoanisole + Phenylboronic acid
Pd(PPh₃)₄, K₂CO₃, THF/H₂O, 80°C
4-Methoxybiphenyl
Bromobenzene + 2-Thienylboronic acid
Pd(PPh₃)₄, Na₂CO₃, DME/H₂O
2-Phenylthiophene
The workhorse of pharmaceutical synthesis for making biaryl compounds. Used in the synthesis of countless drug molecules (e.g., losartan, valsartan).