SuzukiMiyaurareaktionen

The Suzuki-Miyaura reaction is a cross-coupling reaction used in organic chemistry to form carbon-carbon bonds. It involves the reaction between an organoboron compound and an organohalide in the presence of a palladium catalyst and a base. This reaction is highly versatile and has found widespread application in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and materials.

The general scheme of the Suzuki-Miyaura reaction involves the palladium-catalyzed coupling of a boronic acid or boronate ester with an aryl or vinyl halide. The reaction proceeds through a catalytic cycle that typically includes oxidative addition of the organohalide to the palladium catalyst, transmetalation of the organic group from boron to palladium, and reductive elimination to form the new carbon-carbon bond and regenerate the palladium catalyst. The base plays a crucial role in activating the organoboron compound for transmetalation.

One of the key advantages of the Suzuki-Miyaura reaction is its tolerance to a wide range of functional groups, allowing for the synthesis of diverse and complex molecules. Furthermore, the organoboron reagents are generally stable, easy to handle, and less toxic compared to other organometallic reagents. The reaction conditions are often mild, making it suitable for sensitive substrates. Its reliability and efficiency have led to its widespread adoption in both academic research and industrial synthesis, earning its discoverers, Akira Suzuki and Ei-ichi Negishi (who developed related cross-coupling reactions), a share of the Nobel Prize in Chemistry in 2010.