Mild reductive rearrangement of oximes and oxime ethers to secondary amines with hydrosilanes catalyzed by B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>
Huaquan Fang, Guoqiang Wang, Martin Oestreich
Abstract
Oximes, its ether derivatives and the corresponding hydroxylamines rearrange to secondary amines when reacted with PhSiH<sub>3</sub> and B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> as catalyst. Computations suggest a reduction–rearrangement to be slightly favored over a Beckmann-type sequence.
Topics & Concepts
ChemistryBeckmann rearrangementOximeCatalysisEtherMedicinal chemistrySequence (biology)Organic chemistryBiochemistryOrganoboron and organosilicon chemistrySulfur-Based Synthesis TechniquesChemical Synthesis and Reactions