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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Halogenation of carbon substrates for increased reactivity with alkenes
Matthew R Lockett1, Lloyd M Smith
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Abstract:
Carbon substrates are readily functionalized with alkene-containing molecules via an ultraviolet-light-catalyzed reaction, resulting in the formation of a carbon-carbon bond with the surface. This reaction is typically performed on hydrogen-terminated carbon substrates, limiting its utility as alkene molecules with low electron affinities do not readily attach to this surface. Recently, a wet-chemical method for preparing bromine- and chlorine-terminated carbon substrates has been developed. Replacing the terminal hydrogen atoms with a halogen analog increases the surface's reactivity with alkene-containing molecules, affording a means of modifying the carbon substrate with the alkene molecules that do not readily attach to the hydrogen-terminated surface and with a greatly reduced reaction time.
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