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Carbopalladation of C-C σ-bonds enabled by strained boronate complexes

14 December 2018

Research from the Aggarwal Group reveals a new fundamental reactivity mode of palladium complexes

Palladium-mediated cross-couplings are very broadly used chemical transformations. In fact, it has been reported that one third of all pharmaceuticals tested have employed palladium-mediated cross-couplings at some point in their synthesis.

However, palladium mediated processes are restricted to a small number of "allowable" reaction types. A recent paper, published in Nature Chemistry, reports a new fundamental reactivity mode of palladium complexes  – the carbopalladation of C-C s-bonds – which enables the coupling of readily available organoboronic esters and aryl triflates across a cyclobutane unit with total diastereocontrol. The pharmaceutically-relevant 1,1,3-trisubstituted cyclobutane products obtained are decorated with an array of modular building blocks, including a boronic ester which can be readily derivatized.

Further information

Paper:

Carbopalladation of C-C σ-bonds enabled by strained boronate complexes 
Nature Chemistry
Alexander Fawcett, Tobias Biberger and Varinder K. Aggarwal

 

 

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