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

Journal: Angewandte Chemie International Edition

Published: 2020-10-13

DOI: 10.1002/anie.202010251

Affiliations: 2

Authors: 3

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Research Highlight

Connecting carbons without a catalyst

© Science Photo Library/Getty Images

© Science Photo Library/Getty Images

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.

Supported content

  1. Angewandte Chemie International Edition 59, 22460–22464 (2020). doi: 10.1002/anie.202010251
Institutions Share
Kanazawa University (KU), Japan 1
Japan Science and Technology Agency (JST), Japan 0