SuzukiMiyaura

Suzuki–Miyaura coupling, commonly called the Suzuki coupling, is a palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron reagents and organohalides or organotriflates. Developed independently in the late 1970s and early 1980s by Norio Miyaura and Akira Suzuki, the method rapidly became a standard tool in organic synthesis. It is widely used to construct biaryl and vinyl compounds, underpinning the synthesis of pharmaceuticals, natural products, and advanced materials.

The catalytic cycle centers on oxidative addition of the organohalide to a Pd(0) species, transmetalation with a boron partner in the presence of a base, and reductive elimination to release the coupled product and regenerate Pd(0). Boron partners commonly include boronic acids, boronate esters, or trifluoroborates; bases such as potassium phosphate, carbonate, or hydroxide facilitate transmetalation. Typical catalysts employ palladium with phosphine ligands, e.g., Pd(PPh3)4 or more advanced systems to accommodate less reactive substrates.

Substrate scope covers a wide range of aryl-, heteroaryl-, and vinyl-halides or triflates coupled with aryl, vinyl, or alkyl boron reagents. The reaction is notable for broad functional-group tolerance and the use of relatively mild conditions, often in aqueous-organic solvent systems. Aryl chlorides and less reactive substrates may require more active catalysts or special ligands.

The Suzuki–Miyaura coupling is a cornerstone of modern synthetic chemistry and has been pivotal in the production of pharmaceuticals, agrochemicals, and materials. In 2010, Akira Suzuki received the Nobel Prize in Chemistry along with Ei-ichi Negishi and Richard Heck for palladium-catalyzed cross-coupling reactions, including this one.