Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane.

ABSTRACT: Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously ca

SUBMITTER: Buonomo JA 

PROVIDER: S-EPMC5647249 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature