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Cationic Phosphorus Compounds Based on a Bis(1-piperidinyl)-Substituted Carbodiphosphorane: Syntheses, Structures, and C -H Activation. | LitMetric

Cationic Phosphorus Compounds Based on a Bis(1-piperidinyl)-Substituted Carbodiphosphorane: Syntheses, Structures, and C -H Activation.

Organometallics

Chair of Inorganic Chemistry II, Faculty of Chemistry and Biochemistry, Ruhr-University Bochum, Universitätsstraße 150, 44801 Bochum, Germany.

Published: December 2020

AI Article Synopsis

Article Abstract

The use of the bis(1-piperidinyl)-substituted carbodiphosphorane (Ph(Pip)P)C () as an NCN ligand for the stabilization of phosphorus cations was studied. A simple ligand for halide exchange allowed the synthesis and isolation of a series of phosphorus monocations of the type [-PR] (with R = Cl, Br, I, CyCl, Ph). These cations exhibit characteristic NMR and structural properties which nicely correlate with the charge at the central phosphorus atom and the interaction between the ligand and the PR moiety. Halide abstraction from the monocations does not result in isolable dicationic compounds but in an unexpected intramolecular C -H activation in the piperidinyl group. DFT studies show that the selective activation of the CH group next to the nitrogen atom instead of a CH group at the phenyl substituents proceeds via an iminium intermediate formed by hydride transfer from the carbon atom to the cationic phosphorus center. This observation clearly demonstrates the pronounced π acidity of the dicationic phosphorus species in comparison to compounds with a further π-donor substituent.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7861138PMC
http://dx.doi.org/10.1021/acs.organomet.0c00412DOI Listing

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