Transition‐Metal‐Free Cross‐Coupling by Using Tertiary Benzylic Organoboronates

Connecting carbons without a catalyst

31 May 2021

A metal-free method for connecting challenging molecular fragments together could offer an efficient new way to make complex chemicals such as pharmaceutical drugs.

Cross-coupling reactions are a popular way to connect simple organic starting materials together to build a complex target molecule. They typically use a metal catalyst to mediate the formation of a new carbon–carbon bond between the two starting materials.

However, when the carbon atoms to be connected are crowded ‘tertiary’ carbons, the metal-based reaction can be slow and affected by side reactions.

Now, researchers at Kanazawa University in Japan have developed a transition-metal-free cross-coupling reaction to efficiently connect tertiary carbon starting materials together. The protocol uses an organoboronate starting material, which when treated with a base will react with a common starting material called an alkyl halide to form the desired carbon–carbon bond.

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References

1. Angewandte Chemie International Edition 59, 22460–22464 (2020). doi: 10.1002/anie.202010251