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

Research output: Contribution to journalArticle

41 Citations (Scopus)

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
Pages (from-to)1244-1247
Number of pages4
JournalACS Catalysis
Volume7
Issue number2
DOIs
Publication statusPublished - Feb 3 2017

Fingerprint

Lanthanoid Series Elements
Ketones
Rare earth elements
Aldehydes
Nitriles
Catalysts
Alkynes
Alkenes
Functional groups
Rare earths
Olefins
Air

Keywords

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

ASJC Scopus subject areas

  • Catalysis

Cite this

Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst. / Weidner, Victoria L.; Barger, Christopher J.; Delferro, Massimiliano; Lohr, Tracy L.; Marks, Tobin J.

In: ACS Catalysis, Vol. 7, No. 2, 03.02.2017, p. 1244-1247.

Research output: Contribution to journalArticle

Weidner, Victoria L. ; Barger, Christopher J. ; Delferro, Massimiliano ; Lohr, Tracy L. ; Marks, Tobin J. / Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst. In: ACS Catalysis. 2017 ; Vol. 7, No. 2. pp. 1244-1247.
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