Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization

Fidelius, Jannis; Schwedtmann, Kai; Schellhammer, Sebastian; Haberstroh, Jan; Schulz, Stephen; Huang, Rongjuan; Klotzsche, Max C.; Bauzá, Antonio; Frontera, Antonio; Reineke, Sebastian; Weigand, Jan J.

doi:10.1016/j.chempr.2023.10.016

Chem

2024

DOI: 10.1016/j.chempr.2023.10.016

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Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization

Jannis Fidelius,

Kai Schwedtmann,

Sebastian Schellhammer

et al.

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Cited by 5 publications

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Cycloadditionen von Diazoalkenen mit P₄ und tBuCP: Ein Zugang zu Diazaphospholen

Hauer,

Reitz,

Koike

et al. 2024

Angewandte Chemie

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Diazoalkenes readily react with tert‑butylphosphaalkyne (tBuCP) and white phosphorus (P4) to afford novel phosphorus heterocycles, 3H‑1,2,4‐diazamonophospholes and 1,2,3,4‐diazadiphospholes. Both species represent rare examples of neutral heterophospholes. The mechanism of formation and the electronic structures of these formal (3+2) cycloaddition products were analyzed computationally. The new phospholes form structurally diverse coordination compounds with transition metal and main group elements. Given the growing number of stable diazoalkenes, this work offers a straightforward route to neutral aza(di‐)phospholes as a new ligand class.

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Cycloadditionen von Diazoalkenen mit P₄ und tBuCP: Ein Zugang zu Diazaphospholen

Hauer,

Reitz,

Koike

et al. 2024

Angewandte Chemie

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Cycloadditions of Diazoalkenes with P₄ and tBuCP: Access to Diazaphospholes

Hauer,

Reitz,

Koike

et al. 2024

Angew Chem Int Ed

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Pnictogen‐Rich Heterocycles Derived from a Phosphadiazonium Cation

Milkovich,

Buguis,

Boyle

et al. 2024

Chemistry A European J

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Heterocycles that pair main group elements and nitrogen are extremely important within the π‐conjugated materials research community. Compared to the vast number of boron‐nitrogen heterocycles, those that include phosphorus are less common. Furthermore, the use of phosphorus‐nitrogen triple bonds of any type to prepare such compounds is unprecedented. Here, we pair pyridyl hydrazonide ligands with phosphadiazonium cations and demonstrate that the chelated Mes*NP group is directly implicated in the photophysical and redox properties observed for the resulting heterocycles. In doing so, we introduce a novel building block for the production of phosphorus‐containing heterocycles that could find use in small molecule activation and catalysis or as the functional component of emerging organic electronics.

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Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization

Cited by 5 publications

References 53 publications

Cycloadditionen von Diazoalkenen mit P₄ und tBuCP: Ein Zugang zu Diazaphospholen

Cycloadditionen von Diazoalkenen mit P₄ und tBuCP: Ein Zugang zu Diazaphospholen

Cycloadditions of Diazoalkenes with P₄ and tBuCP: Access to Diazaphospholes

Pnictogen‐Rich Heterocycles Derived from a Phosphadiazonium Cation

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Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization

Cited by 5 publications

References 53 publications

Cycloadditionen von Diazoalkenen mit P4 und tBuCP: Ein Zugang zu Diazaphospholen

Cycloadditionen von Diazoalkenen mit P4 und tBuCP: Ein Zugang zu Diazaphospholen

Cycloadditions of Diazoalkenes with P4 and tBuCP: Access to Diazaphospholes

Pnictogen‐Rich Heterocycles Derived from a Phosphadiazonium Cation

Contact Info

Product

Resources

About

Cycloadditionen von Diazoalkenen mit P₄ und tBuCP: Ein Zugang zu Diazaphospholen

Cycloadditionen von Diazoalkenen mit P₄ und tBuCP: Ein Zugang zu Diazaphospholen

Cycloadditions of Diazoalkenes with P₄ and tBuCP: Access to Diazaphospholes