Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

James W. B. Fyfe, Neal J. Fazakerley, Allan J. B. Watson

Research output: Contribution to journalArticle

38 Downloads (Pure)

Abstract

Chemoselective Suzuki-Miyaura cross-coupling generally requires a designed deactivation of one nucleophile towards transmetallation. Here we show that boronic acids can be chemoselectively reacted in the presence of ostensibly equivalently reactive boronic acid pinacol (BPin) esters by kinetic discrimination during transmetallation. Simultaneous electrophile control allows sequential chemoselective cross-couplings in a single operation in the absence of protecting groups.
Original languageEnglish
Number of pages5
JournalAngewandte Chemie International Edition
Publication statusAccepted/In press - 2 Dec 2016

Keywords

  • multinucleophile systems
  • chemical synthesis
  • chemoselectivity
  • organoborons
  • arylboron nucleophiles
  • transmetallation
  • kinetic discrimination
  • Suzuki-Miyaura reaction
  • boron
  • cross-coupling
  • palladium

Fingerprint Dive into the research topics of 'Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation'. Together they form a unique fingerprint.

Cite this