Facile Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation

Daniel J. Scott, Trevor R. Simmons, Elliot J. Lawrence, Gregory G. Wildgoose, Matthew J. Fuchter, Andrew E. Ashley

Research output: Contribution to journalArticle

72 Citations (Scopus)
5 Downloads (Pure)

Abstract

Despite rapid advances in the field of metal-free, “frustrated Lewis pair” (FLP)-catalyzed hydrogenation, the need for strictly anhydrous reaction conditions has hampered wide-scale uptake of this methodology. Herein, we report that, despite the generally perceived moisture sensitivity of FLPs, 1,4-dioxane solutions of B(C6F5)3 actually show appreciable moisture tolerance and can catalyze hydrogenation of a range of weakly basic substrates without the need for rigorously inert conditions. In particular, reactions can be performed directly in commercially available nonanhydrous solvents without subsequent drying or use of internal desiccants.
Original languageEnglish
Pages (from-to)5540-5544
JournalACS Catalysis
Volume5
Issue number9
DOIs
Publication statusPublished - 17 Aug 2015

Keywords

  • “frustrated Lewis pairs”
  • catalytic hydrogenation
  • water tolerance
  • solvent effects
  • metal-free

Cite this