Stereoretentive H/D Exchange via an Electroactivated Heterogeneous Catalyst at sp3 C–H Sites Bearing Amines or Alcohols

Souful Bhatia, Greg Spahlinger, Nehal Boukhumseen, Quentin Boll, Zhenglong Li, James E. Jackson

Research output: Contribution to journalArticle

  • 5 Citations

Abstract

This report describes a mild, aqueous-phase strategy that enables stereoretentive C–H activation at sp3 C–H sites bearing amine or alcohol groups. The transformation utilizes D2O to replace the hydrogen with deuterium while retaining stereochemistry. Electroactivated ruthenium particles, which are supported by an activated carbon cloth (Ru/ACC), catalyze this reaction on a timescale of minutes to hours. This yields optimal results at low current density and mild temperature.

LanguageEnglish (US)
Pages4230-4235
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number24
DOIs
StatePublished - Aug 1 2016

Profile

Bearings (structural)
Stereochemistry
Ruthenium
Deuterium
stereochemistry
activated carbon
low currents
retaining
Activated carbon
ruthenium
Amines
deuterium
Hydrogen
amines
alcohols
Current density
Chemical activation
Alcohols
activation
current density

Keywords

  • C–H activation
  • Deuterium
  • Electrocatalysis
  • Heterogeneous catalysis
  • Stereoretentivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Stereoretentive H/D Exchange via an Electroactivated Heterogeneous Catalyst at sp3 C–H Sites Bearing Amines or Alcohols. / Bhatia, Souful; Spahlinger, Greg; Boukhumseen, Nehal; Boll, Quentin; Li, Zhenglong; Jackson, James E.

In: European Journal of Organic Chemistry, Vol. 2016, No. 24, 01.08.2016, p. 4230-4235.

Research output: Contribution to journalArticle

Bhatia, Souful ; Spahlinger, Greg ; Boukhumseen, Nehal ; Boll, Quentin ; Li, Zhenglong ; Jackson, James E./ Stereoretentive H/D Exchange via an Electroactivated Heterogeneous Catalyst at sp3 C–H Sites Bearing Amines or Alcohols. In: European Journal of Organic Chemistry. 2016 ; Vol. 2016, No. 24. pp. 4230-4235
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