Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls

Ataualpa A.C. Braga, Nelson H. Morgon, Gregori Ujaque, Agustí Lledós, Feliu Maseras

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Abstract

The transmetalation step of the Suzuki-Miyaura cross-coupling between aryl groups is analyzed by means of DFT calculations with the Becke3LYP functional. The halide considered is Ph-Br, and the organoboronic acid is Ph-B(OH)2. The model catalyst is Pd(PH3)2, and the base, OH-. The transmetalation is considered to start from the Pd(Ph)(PH3)2Br complex, the product of the oxidative addition. The results are compared with those of a previous study on the analogous reaction with vinyl groups, and it is shown that the reaction mechanism is very similar. © 2006 Elsevier B.V. All rights reserved.
Original languageEnglish
Pages (from-to)4459-4466
JournalJournal of Organometallic Chemistry
Volume691
Issue number21
DOIs
Publication statusPublished - 15 Oct 2006

Keywords

  • Biaryl
  • Cross-coupling
  • Density functional theory
  • Suzuki-Miyaura reaction
  • Transmetalation

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