Transmetalation in the Suzuki-Miyaura Coupling: The Fork in the Trail

Alastair J. J. Lennox, Guy C. Lloyd-Jones*

*Corresponding author for this work

Research output: Contribution to journalLiterature reviewpeer-review

Abstract / Description of output

The Suzuki-Miyaura coupling is one of the few transition-metal-catalyzed CC bond-forming reactions that have been used in applications ranging from discovery chemistry to manufacturing processes. Although coupling proceeds through the generic three-stage oxidative addition, transmetalation, reductive elimination' sequence, there are a number of features that differentiate the Suzuki-Miyaura process from other transition-metal-catalyzed cross-couplings. Most of these features are centered around, or are a consequence of, activation of the boron reagent for transmetalation through one or both of two distinct pathways. This review focuses on the evidence that has been presented for this fork in the trail, and the potential to apply such mechanistic insight to the design of reaction conditions.

Original languageEnglish
Pages (from-to)7362-7370
Number of pages9
JournalAngewandte Chemie International Edition
Volume52
Issue number29
DOIs
Publication statusPublished - 15 Jul 2013

Keywords / Materials (for Non-textual outputs)

  • boron
  • cross coupling
  • palladium
  • reaction mechanisms
  • transmetalation
  • ARYLBORONIC ACIDS
  • ORGANOBORON COMPOUNDS
  • BORONIC ACID
  • STEREOSELECTIVE-SYNTHESIS
  • CATALYZED REACTION
  • TRIPLE ROLE
  • PALLADIUM
  • ARYL
  • COMPLEXES
  • BASE

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