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Content archived on 2024-06-18

Fundamentally new strategy for coupling of secondary alkyl boronic esters for the formation of new C-C bonds

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A new method for linking carbon atoms

Researchers in the EU have developed a new method to link carbon atoms together that will allow synthesis of a whole new category of molecules.

Carbon-carbon (C-C) bonds are one of the most important molecular bonds in organic chemistry. Carbon atoms can join together in a number of ways, but some are more difficult to complete as part of an industrial reaction. The EU-funded FUNTASTIC (Fundamentally new strategy for coupling of secondary alkyl boronic esters for the formation of new C-C bonds) project found a promising way to create a difficult type of C-C bond, and developed it into a reliable method for industrial chemical synthesis. The method, which is known as cross-coupling, is catalysed by palladium, a catalyst commonly used for chemical synthesis. The method could also yield valuable by-products that could be used for other industrial processes. Researchers initially demonstrated their method using a common starting product called DDQ, which produced a high yield in a short space of time. With this completed, they moved on to testing a range of starting materials and process conditions. Testing different starting compounds showed researchers the flexibility of this new reaction. One of the substrates is quite flexible, while the other needs to be a very specific type of molecule. FUNTASTIC also investigated different reaction conditions to optimise the overall process. Researchers also used computer simulations to confirm the theoretical limits of the reaction. Cross-coupling has been used industrially to form different C-C bonds for years. With these findings, cross-coupling can now produce many more chemical products than before.

Keywords

Carbon atoms, carbon-carbon, organic chemistry, chemical synthesis, cross-coupling

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