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Instantaneous SmI 2 /H 2 O/Amine‐Mediated Reductions in THF
Author(s) -
Dahlén Anders,
Hilmersson Göran
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390129
Subject(s) - chemistry , amine gas treating , medicinal chemistry , sulfur , nitrogen , kinetic isotope effect , oxygen , beta (programming language) , organic chemistry , deuterium , physics , quantum mechanics , computer science , programming language
The SmI 2 ‐mediated reductions of ketones, imines, and α , β ‐unsaturated esters have been shown to be instantaneous in the presence of H 2 O and an amine in THF. The SmI 2 ‐mediated reductions are not only shown to be fast and quantitative by the addition of H 2 O and an amine, but the workup procedures are also simplified. Competing experiments with SmI 2 /H 2 O/amine confirmed that α , β ‐unsaturated esters could be selectively reduced in the presence of ketones or imines. Comparison of analogue ligands showed that nitrogen and phosphorus ligands are superior to oxygen and sulfur ligands in these reductions. The trialkylphosphine 1,2‐bis(dimethylphosphino)ethane (DMPE) provided a primary kinetic isotope effect, yielding a k H / k D of 4.5.