KHMDS enhanced SmI(2)-mediated reformatsky type alpha-cyanation.
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.
Ankner
Tobias
T
Department of Chemistry, University of Gothenburg, Göteborg, Sweden.
Fridén-Saxin
Maria
M
Pemberton
Nils
N
Seifert
Tina
T
Grøtli
Morten
M
Luthman
Kristina
K
Hilmersson
Göran
G