Speciation control during Suzuki-Miyaura cross-coupling of haloaryl and haloalkenyl MIDA boronic esters

James W. B. Fyfe, Elena Valverde, Ciaran P. Seath, Alan R. Kennedy, Joanna M. Redmond, Niall A. Anderson, Allan J. B. Watson

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Abstract

Boronic acid solution speciation can be controlled during the Suzuki-Miyaura cross-coupling of haloaryl MIDA boronic esters to enable the formal homologation of boronic acid derivatives. The reaction is contingent upon control of the basic biphase and is thermodynamically driven: temperature control provides highly chemoselective access to either BMIDA adducts at room temperature or BPin products at elevated temperature. Control experiments and solubility analyses have provided some insight into the mechanistic operation of the formal homologation process.
Original languageEnglish
Pages (from-to)8951–8964
Number of pages14
JournalChemistry - A European Journal
Volume21
Issue number24
Early online date8 May 2015
DOIs
Publication statusPublished - 8 Jun 2015

Keywords

  • boron
  • chemoselectivity
  • cross-coupling
  • palladium
  • speciation

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    Fyfe, J. W. B., Valverde, E., Seath, C. P., Kennedy, A. R., Redmond, J. M., Anderson, N. A., & Watson, A. J. B. (2015). Speciation control during Suzuki-Miyaura cross-coupling of haloaryl and haloalkenyl MIDA boronic esters. Chemistry - A European Journal, 21(24), 8951–8964. https://doi.org/10.1002/chem.201500970