Reduction of 2-<i>H</i>-substituted pyrrolinium cations: the carbon–carbon single bond in air stable 2,2′-bipyrrolidines as a two-electron-source

Nayak, Mithilesh Kumar; Elvers, Benedict J.; Mandal, Debdeep; Das, Ayan; Ramakrishnan, Raghunathan; Mote, Kaustubh R.; Schulzke, Carola; Yildiz, Cem B.; Jana, Anukul

doi:10.1039/d3cc00891f

Chem. Commun.

2023

DOI: 10.1039/d3cc00891f

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Reduction of 2-H-substituted pyrrolinium cations: the carbon–carbon single bond in air stable 2,2′-bipyrrolidines as a two-electron-source

Mithilesh Kumar Nayak

Benedict J. Elvers

Debdeep Mandal

et al.

Abstract: Reduction of 2-H-substituted pyrrolinium cations via initially formed secondary radicals results in either dimerisation or H-abstracted products while the outcome depends on the N-substituents. The resultant central carbon-carbon single bond...

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2024

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Cited by 3 publications

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“Inverted” Cyclic(Alkyl)(Amino)Carbene (CAAC) Ruthenium Complex Catalyzed Isomerization Metathesis (ISOMET) of Long Chain Olefins to Propylene at Low Ethylene Pressure

Farkas,

Csókás,

Erdélyi

et al. 2024

Advanced Science

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Isomerization Metathesis (ISOMET) reaction is an emerging tool for “open loop” chemical recycling of polyethylene to propylene. Novel, latent N‐Alkyl substituted Cyclic(Alkyl)(Amino)Carbene (CAAC)–ruthenium catalysts (5a‐Ru, 3b‐Ru – 6c‐Ru) are developed rendering “inverted” chemical structure while showing enhanced ISOMET activity in combination with (RuHCl)(CO)(PPh3)3 (RuH) double bond isomerization co‐catalyst. Systematic investigations reveal that the steric hindrance of the substituents on nitrogen and carbon atom adjacent to carbene moiety in the CAAC ligand have significantly improved the catalytic activity and robustness. In contrast to the NHC‐Ru and CAAC‐Ru catalyst systems known so far, these systems show higher isomerization metathesis (ISOMET) activity (TON: 7400) on the model compound 1‐octadecene at as low as 3.0 bar optimized pressure, using technical grade (3.0) ethylene. The propylene content formed in the gas phase can reach up to 20% by volume.

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“Inverted” Cyclic(Alkyl)(Amino)Carbene (CAAC) Ruthenium Complex Catalyzed Isomerization Metathesis (ISOMET) of Long Chain Olefins to Propylene at Low Ethylene Pressure

Farkas,

Csókás,

Erdélyi

et al. 2024

Advanced Science

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Synthese und Reaktivität dreifach koordinierter Organoberylliumazide

Czernetzki,

Kunz,

Huynh

et al. 2024

Angewandte Chemie

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A series of terminal mono‐ and disubstituted beryllium azides of the form [(CAAC)Be(N3)R] (R = CAACH, Dur; CAACH / CAAC = 1‐(2,6‐diisopropylphenyl)‐3,3,5,5‐tetramethylpyrrolidin‐2‐yl/idene, Dur = 2,3,5,6‐tetramethylphenyl) and [L2Be(N3)2] (L = CAACNH = 1‐(2,6‐diisopropylphenyl)‐3,3,5,5‐tetramethylpyrrolidin‐2‐imine, IiPrMe = 1,3‐diisopropyl‐4,5‐dimethylimidazol‐2‐ylidene), respectively, were synthesized and characterized by NMR spectroscopy and X‐ray crystallography. Thermolysis and photolysis products of these first examples of tricoordinate azidoberyllium complexes evidence extensive ligand scrambling and the formal insertion of nitrenes into the CAAC‒Be bond, generating cyclic alkyl(amino)imine (CAAI) ligands. Furthermore, the reaction with a small N‐heterocyclic carbene (NHC) leads to unexpected CAAC‐NHC ligand exchange, while the reaction with pentaphenylborole yields the first γ‐azide adduct of a borole, long postulated to be the first step in the synthesis of 1,2‐azaborinines from boroles and azides.

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Synthesis and Reactivity of Tricoordinate Organoberyllium Azides

Czernetzki,

Kunz,

Huynh

et al. 2024

Angew Chem Int Ed

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Reduction of 2-H-substituted pyrrolinium cations: the carbon–carbon single bond in air stable 2,2′-bipyrrolidines as a two-electron-source

Abstract: Reduction of 2-H-substituted pyrrolinium cations via initially formed secondary radicals results in either dimerisation or H-abstracted products while the outcome depends on the N-substituents. The resultant central carbon-carbon single bond...

Cited by 3 publications

References 39 publications

“Inverted” Cyclic(Alkyl)(Amino)Carbene (CAAC) Ruthenium Complex Catalyzed Isomerization Metathesis (ISOMET) of Long Chain Olefins to Propylene at Low Ethylene Pressure

“Inverted” Cyclic(Alkyl)(Amino)Carbene (CAAC) Ruthenium Complex Catalyzed Isomerization Metathesis (ISOMET) of Long Chain Olefins to Propylene at Low Ethylene Pressure

Synthese und Reaktivität dreifach koordinierter Organoberylliumazide

Synthesis and Reactivity of Tricoordinate Organoberyllium Azides

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