The transmetalation process in Suzuki-Miyaura reactions: Calculations indicate lower barrier via boronate intermediate

Manuel A. Ortuño, Agustí Lledós, Feliu Maseras, Gregori Ujaque

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

Recent experimental reports have called into question the validity of the boronate mechanism (through a R-B(OH3- intermediate) for the transmetalation step in the Suzuki-Miyaura cross-coupling, favoring instead the palladium hydroxo pathway (through an [LnPd(R′)(OH)] intermediate). Herein we report DFT calculations with the M06 functional performed on realistic model systems, including a combination of explicit solvent molecules along with a continuum method. These computational results support the boronate mechanism. The mechanistic proposal is shown to be compatible with the available experimental evidence.

Original languageEnglish (US)
Pages (from-to)3132-3138
Number of pages7
JournalChemCatChem
Volume6
Issue number11
DOIs
StatePublished - Nov 2014

Keywords

  • Boranes
  • Cross-coupling
  • Density functional calculations
  • Palladium
  • Transition states

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