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: Research - peer-reviewArticle

    • 3 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

    stereochemistry
    activated carbon
    low currents
    retaining
    ruthenium
    deuterium
    amines
    alcohols
    activation
    current density
    catalysts
    hydrogen
    temperature
    Bearings (structural)
    Stereochemistry
    Ruthenium
    Deuterium
    Activated carbon
    Amines
    Hydrogen

    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: Research - peer-reviewArticle

    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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