Nitrous oxide as diazo transfer reagent

Genoux, Alexandre; Severin, Kay

doi:10.1039/d4sc04530k

Chem. Sci.

2024

DOI: 10.1039/d4sc04530k

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Nitrous oxide as diazo transfer reagent

Alexandre Genoux,

Kay Severin

Abstract: The review summarizes the use of nitrous oxide (N2O, ‘laughing gas’) as a diazo transfer reagent in synthetic chemistry.

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Cited by 6 publications

References 177 publications

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Spaltung von Carbodicarbenen mit N₂O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

He,

Lyu,

Tymann

et al. 2024

Angewandte Chemie

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Die Spaltung von Carbophosphinocarbenen und Carbodicarbenen mit Distickstoffmonoxid (N2O) führt zur Bildung von raumtemperaturstabilen Diazoalkenen. Die Nützlichkeit von Ph3P/N2 und NHC/N2 Ligandenaustauschreaktionen wurde durch den Zugang zu neuartigen Benzimidazol‐ und Benzothiazol‐abgeleiteten Diazoalkenen demonstriert, die mit den derzeit üblichen Methoden nicht zugänglich sind. Die stabilen Diazoalkene ermöglichen anschließend weitere Ligandenaustauschreaktionen an einem C(0)‐Zentrum mit Kohlenmonoxid, Isocyanid oder einem Diamidocarben (DAC). Insgesamt ermöglicht die Kombination von bisher unbekannten NHC/N2 und N2/L (L = DAC, CO, R−NC) Ligandenaustauschreaktionen an einem C(0)‐Zentrum die selektive Funktionalisierung der Carbodicarben‐Ligandenstruktur, was eine neue Methode zum schnellen Aufbau neuartiger Carbodicarbene oder Cumulenverbindungen darstellt.

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Spaltung von Carbodicarbenen mit N₂O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

He,

Lyu,

Tymann

et al. 2024

Angewandte Chemie

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An Isolable Base‐Stabilized Diazosilenyl Cation

Takahashi,

Rodríguez‐Álvarez,

Baceiredo

et al. 2024

Angewandte Chemie

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Cleavage of Carbodicarbenes with N₂O for Accessing Stable Diazoalkenes: Two‐Fold Ligand Exchange at a C(0)‐Atom

He,

Lyu,

Tymann

et al. 2024

Angew Chem Int Ed

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The cleavage of carbophosphinocarbenes and carbodicarbenes with nitrous oxide (N2O) leads to the formation of room‐temperature stable diazoalkenes. The utility of Ph3P/N2 and NHC/N2 ligand exchange reactions were demonstrated by accessing novel benzimidazole‐ and benzothiazole derived diazoalkenes, which are not accessible by the current state‐of‐the‐art methods. The stable diazoalkenes subsequently allow further ligand exchange reactions at C(0) with carbon monoxide, isocyanide, or a diamidocarbene (DAC). Overall, the combination of hitherto unknown NHC/N2 and N2/L (L = DAC, CO, R−NC) ligand exchange reactions at a C(0) center allow the selective functionalization of the carbodicarbene ligand structure which represents a new methodology to rapidly assemble novel carbodicarbenes or cumulenic compounds.

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Nitrous oxide as diazo transfer reagent

Abstract: The review summarizes the use of nitrous oxide (N2O, ‘laughing gas’) as a diazo transfer reagent in synthetic chemistry.

Cited by 6 publications

References 177 publications

Spaltung von Carbodicarbenen mit N₂O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

Spaltung von Carbodicarbenen mit N₂O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

An Isolable Base‐Stabilized Diazosilenyl Cation

Cleavage of Carbodicarbenes with N₂O for Accessing Stable Diazoalkenes: Two‐Fold Ligand Exchange at a C(0)‐Atom

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Nitrous oxide as diazo transfer reagent

Abstract: The review summarizes the use of nitrous oxide (N2O, ‘laughing gas’) as a diazo transfer reagent in synthetic chemistry.

Cited by 6 publications

References 177 publications

Spaltung von Carbodicarbenen mit N2O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

Spaltung von Carbodicarbenen mit N2O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

An Isolable Base‐Stabilized Diazosilenyl Cation

Cleavage of Carbodicarbenes with N2O for Accessing Stable Diazoalkenes: Two‐Fold Ligand Exchange at a C(0)‐Atom

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Product

Resources

About

Spaltung von Carbodicarbenen mit N₂O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

Spaltung von Carbodicarbenen mit N₂O zu stabilen Diazoalkenen: Zweifacher Ligandenaustausch an einem C(0)‐Atom

Cleavage of Carbodicarbenes with N₂O for Accessing Stable Diazoalkenes: Two‐Fold Ligand Exchange at a C(0)‐Atom