Intramolecular C-N bond activation by a geometrically constrained P-centre.

Chem Commun (Camb)

School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel.

Published: November 2022

AI Article Synopsis

  • The study presents the first instances of activating C-N bonds by inserting them into a restricted phosphorus (P) center.
  • The research examines the processes behind these activations to create new phosphorus compounds using both experimental methods and computational simulations.
  • Notably, when the P center interacts with an N-C(O)H bond, it likely creates an unstable intermediate that subsequently breaks down in the presence of a small amount of HCl, resulting in a hydrophosphorane compound.

Article Abstract

In this work the first examples of C-N bond activation by insertion into a geometrically constrained P-centre are shown. The mechanisms of these activation processes leading to new P species were studied both experimentally and computationally. Interestingly, in the case of insertion of the P-centre into an N-C(O)H bond, an unstable phosphoranyl-formaldehyde intermediate is probably formed, which undergoes decarbonylation in the presence of a catalytic amount of HCl producing a hydrophosphorane.

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Source
http://dx.doi.org/10.1039/d2cc04359aDOI Listing

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