Angewandte Chemie International Edition · 2017 · 59 citations · 38 references
Natural SciencesChemistryInorganic ChemistryOrganic ChemistryOrganometallic ChemistryAddition ReactionsHeterocycle SynthesisHeterocyclic ChemistryReaction PathwaysCarbene Insertion ReactionsHeterocycle ReactivityHeterocyclic ReactivityInsertion ReactionsLewis Acid CatalysisLewis AcidityOrganic SubstratesPhosphine Reactivity
Abstract Phosphinidenes [R‐P] are convenient P 1 building blocks for the synthesis of a plethora of organophosphorus compounds. Thus far, transition‐metal‐complexed phosphinidenes have been used for their singlet ground‐state reactivity to promote selective addition and insertion reactions. One disadvantage of this approach is that after transfer of the P 1 moiety to the substrate, a challenging demetallation step is required to provide the free phosphine. We report a simple method that enables the Lewis acid promoted transfer of phenylphosphinidene, [PhP], from NHC=PPh adducts (NHC=N‐heterocyclic carbene) to various substrates to produce directly uncoordinated phosphorus heterocycles that are difficult to obtain otherwise.
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An overview of N-heterocyclic carbenes
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