Why do silanes reduce electron-rich phosphine oxides faster than electron-poor phosphine oxides?
Alicia M. Kirk, Christopher J. O’Brien, Elizabeth H. Krenske
Abstract
Organophosphine-mediated reactions that generate P[double bond, length as m-dash]O-bonded byproducts can be transformed into catalytic processes by reducing the R3P[double bond, length as m-dash]O byproduct back to PR3in situ with a silane. DFT calculations explain why the most readily reduced phosphine oxides are those incorporating electron-rich (e.g. alkyl) substituents rather than electron-deficient (e.g. aryl) substituents.
Topics & Concepts
SilanesPhosphineSilaneArylChemistryAlkylCatalysisDouble bondElectronPhotochemistryMedicinal chemistryOrganic chemistryPhysicsQuantum mechanicsOrganoboron and organosilicon chemistrySynthetic Organic Chemistry MethodsSynthesis and characterization of novel inorganic/organometallic compounds