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February 28, 2007Journal of the American Chemical Society

Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki−Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters

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Authors

KBKelvin L. BillingsleySBStephen L. Buchwald

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Overview

Experimental study demonstrates high-yield cross-coupling of challenging heteroaryl halides using monophosphine-palladium catalysts, indicating an efficient route to diverse heterobiaryls.

Key Points

  • Develop an active and efficient palladium catalyst system utilizing monophosphine ligands for the Suzuki-Miyaura cross-coupling of heteroaryl halides with heteroaryl boronic acids and esters.
  • Formulated a catalyst system using a palladium precatalyst combined with specific monophosphine ligands.
  • Tested cross-coupling across diverse substrates including heteroaryl boronic acids, boronic esters, heteroaryl chlorides, and sterically hindered halides.
  • Investigated heterocyclic structural factors influencing reaction efficiency.
  • Enabled the preparation of a broad array of heterobiaryl products in good to excellent yields.
  • Demonstrated high catalytic activity toward typically unreactive heteroaryl chlorides and hindered aryl or heteroaryl halides.

Cite This Study

Billingsley et al. (2007) studied this question.

synapsesocial.com/papers/6a1f3ce7742cc02e70833848https://doi.org/10.1021/ja068577p
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