Chemoselective reduction of the phosphoryl bond of O-alkyl phosphinates and related compounds: an apparently impossible transformation

Chemoselective reduction of the phosphoryl bond of O-alkyl phosphinates and related compounds: an apparently impossible transformation

A method is reported for the phosphoryl bond cleavage of O-alkyl phosphinates, phosphinothioates and certain phosphonamidates to furnish the corresponding P(III) borane adducts. The two-step procedure relies upon initial activation of the phosphoryl bond with an alkyl triflate, followed by reduction...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (92), p.16561-16564
Hauptverfasser: Kenny, Niall P, Rajendran, Kamalraj V, Gilheany, Declan G
Format: Artikel
Sprache:eng
Schlagworte:
Activation
Bonding
Boranes
Borohydrides
Cleavage
Lithium
Reduction
Transformations
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Zusammenfassung:A method is reported for the phosphoryl bond cleavage of O-alkyl phosphinates, phosphinothioates and certain phosphonamidates to furnish the corresponding P(III) borane adducts. The two-step procedure relies upon initial activation of the phosphoryl bond with an alkyl triflate, followed by reduction of the resulting intermediate using lithium borohydride.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc06389b