4.4 Article

Dual Ligand-Enabled Late-Stage Fujiwara-Moritani Reactions

Journal

SYNLETT
Volume 33, Issue 4, Pages 357-360

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706014

Keywords

C-H bond activation; late-stage functionalization; palladium catalysis; arenes; Fujiwara-Moritani reaction; olefination

Funding

  1. DFG (Emmy Noether Programme)
  2. Westfalische Wilhelms-Universitat Munster

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In this study, dual ligand-based palladium catalysts were used for late-stage olefination of arenes, successfully functionalizing complex arene substrates. The method utilizes the arene as a limiting reactant and controls the regioselectivity of the transformation by the steric and electronic properties of the substrate, providing a new pathway for preparing regioisomers.
In this study, we describe the use of dual ligand-based palladium catalysts for the late-stage olefination of arenes. Building upon a method previously developed for simple arenes, a variety of complex arene substrates were functionalized. Importantly, the method uses the arene as a limiting reactant and is therefore suitable for valuable starting materials that cannot be used in excess. The regioselectivity of the transformation is controlled by the steric and electronic properties of the substrate, providing access to regioisomers that would be challenging to prepare through other synthetic approaches.

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