Borane-Catalysed Hydroboration of Alkynes and Alkenes

Nate W. J. Ang, Cornelia S. Buettner, Scott Docherty, Alessandro Bismuto, Jonathan R. Carney, Jamie H. Docherty, Michael J. Cowley, Stephen P. Thomas*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

Simple, commercially available borane adducts, H3B center dot THF and H3B center dot SMe2, have been used to catalyse the hydroboration of alkynes and alkenes with pinacolborane to give the alkenyl and alkyl boronic esters, respectively. Alkynes and terminal alkenes underwent highly regioselective hydroboration to give the linear boronic ester products. Good functional group tolerance was observed for substrates bearing ester, amine, ether and halide substituents. This catalytic process shows comparable reactivity to transition-metal-catalysed hydroboration protocols.

Original languageEnglish
Pages (from-to)803-808
Number of pages6
JournalSynthesis: Journal of Synthetic Organic Chemistry
Volume50
Issue number4
Early online date20 Nov 2017
DOIs
Publication statusE-pub ahead of print - 20 Nov 2017

Keywords / Materials (for Non-textual outputs)

  • borane
  • hydroboration
  • alkynes
  • alkenes
  • main-group
  • catalysis
  • PINACOLBORANE
  • B(C6F5)(3)
  • TITANIUM
  • KETONES
  • BORON

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