Umicore launches first cross-coupling catalyst system invented by Prof. Bradley Carrow

Umicore‘s business unit Precious Metals Chemistry is further expanding its cross-coupling catalyst portfolio by launching the tris(1-adamantyl)phosphine ligand: one of the bulkiest, most σ-donating phosphines one could imagine. It is part of the technology invented by Professor Carrow that Umicore licensed from Princeton University.

Cross-coupling reactions have become essential for their versatility and efficiency in the synthesis of agrochemicals, electronic chemicals, fine chemicals or pharmaceuticals. Prof. Bradley Carrow has spent several years trying to understand how to make Pd-catalyzed reactions as efficient as possible, and it has led his group to synthesize bulky tris(1-adamantyl)phosphine. 

Good ligands for cross-coupling reactions tend to be bulky and electron-rich. Tris(1-adamantyl)phosphine is no exception. When used in combination with an active Pd precatalyst, this ligand enables Suzuki-Miyaura couplings between functionalized molecules with turnover numbers approaching 20,000. This translates to Pd loadings as low as 50 ppm achieving high conversion.

The impact of low catalyst loading is twofold. Less Pd metal is required, reducing the impact of its high value to the process. And less Pd to begin with means less Pd that must be removed from the product in order to meet regulatory guidelines in many life science applications. This may simplify the downstream steps required to isolate a clean product.

Umicore now offers its customers worldwide the tris(1-adamantyl)phosphine ligand and relevant active Pd precatalysts on research and commercial scale. Research quantities are available from our distribution partner Merck/MilliporeSigma. 

Please note that depending on the region of publication:    

• MilliporeSigma should be used in Canada and the USA    
• Merck should be used in the rest of the world.