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Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds

Handoko Handoko, Zacharia Benslimane, Paramjit S. Arora

2020Organic Letters50 citationsDOI

Abstract

We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.

Topics & Concepts

DiselenideChemistrySurface modificationCatalysisNucleophileStereospecificityCombinatorial chemistryCatalytic cycleSeleniumDiphenyl diselenideOrganic chemistryPhysical chemistryOrganophosphorus compounds synthesisSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions
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