Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst

Victoria L. Weidner, Christopher J. Barger, Massimiliano Delferro, Tracy L. Lohr*, Tobin J. Marks

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

76 Scopus citations

Abstract

Rapid, clean hydroboration of ketones and aldehydes with HBpin is achieved using the homoleptic rare-earth catalyst La[N(SiMe3)2]3 (LaNTMS). The reaction employs low catalyst loadings (0.01-1 mol % LaNTMS), proceeds rapidly (>99% in 5 min) at 25 °C, and is moderately air-tolerant. Additionally, this hydroboration has good functional group compatibility, including halides, nitro groups, and nitriles, and is exclusively carbonyl-selective in the presence of alkenes and alkynes.

Original languageEnglish (US)
Pages (from-to)1244-1247
Number of pages4
JournalACS Catalysis
Volume7
Issue number2
DOIs
StatePublished - Feb 3 2017

Keywords

  • carbonyl hydroboration
  • chemoselective hydroboration
  • homogeneous catalysis
  • ketone/aldehyde reduction
  • lanthanide

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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