Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds
- 16 July 2020
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 22 (15) , 5811-5816
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.Keywords
Funding Information
- National Science Foundation (CHE-1807670)
This publication has 40 references indexed in Scilit:
- Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonatesChemical Communications, 2013
- Phosphoramidate Tantalum Complexes for Room‐Temperature C-H Functionalization: Hydroaminoalkylation CatalysisAngewandte Chemie International Edition, 2013
- Synthesis of new organophosphorus compounds using the atherton–todd reaction as a versatile toolHeteroatom Chemistry, 2012
- Lewis Base Catalysis in Organic SynthesisAngewandte Chemie International Edition, 2008
- Amifostine: The First Selective-Target and Broad-Spectrum RadioprotectorThe Oncologist, 2007
- Resorcinol bis(diphenyl phosphate), a non‐halogen flame‐retardant additiveJournal of Vinyl and Additive Technology, 1997
- Selenium-77 nuclear magnetic resonance spectroscopyProgress in Nuclear Magnetic Resonance Spectroscopy, 1995
- Investigation Of The Reaction Between Dialkylphosphine Oxides And CarbontetrachloridePhosphorus and Sulfur and the Related Elements, 1986
- The Preparation and Properties of Tertiary and Secondary Phosphine Oxides.Chemical Reviews, 1960
- 129. Studies on phosphorylation. Part III. Further observations on the reaction of phosphites with polyhalogen compounds in presence of bases and its application to the phosphorylation of alcoholsJournal of the Chemical Society (Resumed), 1947