Annellated 1,3,4,2-Triazaphospholenes-Simple Modular Synthesis and a First Exploration of Ligand Properties

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Richter, F.; Birchall, N.; Feil, C.M.; Nieger, M.; Gudat, D. Annellated 1,3,4,2-Triazaphospholenes-Simple Modular Synthesis and a First Exploration of Ligand Properties. Molecules 2022, 27, 4747.

Title: Annellated 1,3,4,2-Triazaphospholenes-Simple Modular Synthesis and a First Exploration of Ligand Properties
Author: Richter, Ferdinand; Birchall, Nicholas; Feil, Christoph M.; Nieger, Martin; Gudat, Dietrich
Publisher: Multidisciplinary Digital Publishing Institute
Date: 2022-07-25
URI: http://hdl.handle.net/10138/346428
Abstract: The successful use of 1,3,4,2-triazaphospholenes (TAPs) as organo-catalysts stresses the need for efficient synthetic routes to these molecules. In this study, we establish the [1 + 4]-cycloaddition of PBr<sub>3</sub> to azo-pyridines as a new approach to preparing pyrido-annellated TAPs in a single step from easily available precursors. The modular assembly of the azo-component via condensation of primary amines and nitroso compounds along with the feasibility of post-functionalization at the P&ndash;Br bond under conservation of the heterocyclic structure allows, in principle, to address a wide range of target molecules, which is illustrated by prototypical examples. The successful synthesis of a transition metal complex confirms for the first time the ability of a TAP to act as a P-donor ligand. Crystallographic studies suggest that hyperconjugation effects and intermolecular interactions induce a qualitatively similar ionic polarization of the P&ndash;Br bonds in TAPs as in better known isoelectronic diazaphospholenes.


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