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Article

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

by
Ferdinand Richter
1,
Nicholas Birchall
1,
Christoph M. Feil
1,
Martin Nieger
2 and
Dietrich Gudat
1,*
1
Institut für Anorganische Chemie, University of Stuttgart, 70550 Stuttgart, Germany
2
Department of Chemistry, University of Helsinki, FIN-00014 Helsinki, Finland
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(15), 4747; https://doi.org/10.3390/molecules27154747
Submission received: 13 July 2022 / Revised: 22 July 2022 / Accepted: 22 July 2022 / Published: 25 July 2022
(This article belongs to the Section Inorganic Chemistry)
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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 PBr3 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–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–Br bonds in TAPs as in better known isoelectronic diazaphospholenes.
Keywords: phosphorus nitrogen heterocycles; [1 + 4]-cycloaddition; N-heterocyclic phosphines; phosphine complexes; P-donor ligands phosphorus nitrogen heterocycles; [1 + 4]-cycloaddition; N-heterocyclic phosphines; phosphine complexes; P-donor ligands
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MDPI and ACS Style

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. https://doi.org/10.3390/molecules27154747

AMA Style

Richter F, Birchall N, Feil CM, Nieger M, Gudat D. Annellated 1,3,4,2-Triazaphospholenes-Simple Modular Synthesis and a First Exploration of Ligand Properties. Molecules. 2022; 27(15):4747. https://doi.org/10.3390/molecules27154747

Chicago/Turabian Style

Richter, Ferdinand, Nicholas Birchall, Christoph M. Feil, Martin Nieger, and Dietrich Gudat. 2022. "Annellated 1,3,4,2-Triazaphospholenes-Simple Modular Synthesis and a First Exploration of Ligand Properties" Molecules 27, no. 15: 4747. https://doi.org/10.3390/molecules27154747

APA Style

Richter, F., Birchall, N., Feil, C. M., Nieger, M., & Gudat, D. (2022). Annellated 1,3,4,2-Triazaphospholenes-Simple Modular Synthesis and a First Exploration of Ligand Properties. Molecules, 27(15), 4747. https://doi.org/10.3390/molecules27154747

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