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Published on: July 19, 2019
KHMDS enhanced SmI(2)-mediated reformatsky type alpha-cyanation
Tobias Ankner1, Maria Fridén-Saxin, Nils Pemberton
1Department of Chemistry, University of Gothenburg, Göteborg, Sweden.
Abstract:
A novel combination of SmI(2), KHMDS, and TsCN can be utilized to introduce a cyano group into structurally diverse and highly sensitive 2-alkyl-chroman-4-ones. Subsequent oxidation allows the formed 2-alkyl-3-cyanochromones to be isolated in yields ranging from 49 to 77%. In addition, alpha-bromoketones and esters were found to undergo equally effective alpha-cyanation.
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