Propellane: von chemischen Kuriositäten zu “explosiven” Materialen und Naturstoffen

Dilmaç, Alicia M.; Spuling, Eduard; Meijere, Armin de; Bräse, Stefan

doi:10.1002/ange.201603951

Cited by 35 publications

(2 citation statements)

References 353 publications

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“…During the past decade, transition‐metalcatalyzed C−H functionalization has emerged as versatile protocol in synthetic organic chemistry, [1] material sciences [2] and medicinal chemistry [3] due to its step and atom economy. In this regime, directing groups (DGs) are initially designed to resolve the regio‐selectivity and improve the catalytic activity of metal [4] .…”

Section: Introductionmentioning

confidence: 99%

Rhodium(III)‐Catalyzed Divergent C−H Functionalization of N‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts

Ren

Yang

et al. 2023

Adv Synth Catal

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We described an Rhodium(III)-catalyzed divergent CÀ H bond functionalization of N-aryl amidines with iodonium ylides. Carbazolones and zwitterionic salts were diversely constructed through intermolecular annulation and intramolecular proton transfer under the different reaction conditions. This protocol is operationally simple and tolerates a variety of functional groups. The efficient post-modification of pharmaceutical molecules demonstrates its practicability.

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Section: Introductionmentioning

confidence: 99%

Rhodium(III)‐Catalyzed Divergent C−H Functionalization of N‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts

Ren

Yang

et al. 2023

Adv Synth Catal

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“…BCP is the smallest member of the bicyclic alkane family, in terms of actual size rather than in terms of atoms present. Indeed, BCP exhibits the shortest non‐bonded distance between bridgehead carbon atoms of 1.85 Å, which is closer in bond length to ethyne (1.20 Å) . The 3D, compact, electronically isolating, and saturated structures of cubane and BCP enable them to avoid undesirable π–π stacking which may lead to improved solubility of chromophoric arrays.…”

Section: Introductionmentioning

confidence: 99%

Bridging and Conformational Control of Porphyrin Units through Non‐Traditional Rigid Scaffolds

Grover

Locke

Flanagan

et al. 2020

Chemistry A European J

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Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally diverse multi‐porphyrin arrays that incorporate the non‐traditional rigid linker groups cubane and bicyclo[1.1.1]pentane (BCP) is described. A robust, reliable, and versatile synthetic procedure was employed to access porphyrin‐cubane/BCP‐porphyrin arrays, representing the largest non‐polymeric structures available for cubane/BCP derivatives. These reactions demonstrate considerable substrate scope, from utilization of small phenyl moieties to large porphyrin rings, with varying lengths and different angles. To control conformational flexibility, amide bonds were introduced between the bridgehead carbon of BCP/cubane and the porphyrin rings. Through varying the orientation of the substituents around the amide bond of cubane/BCP, different intermolecular interactions were identified through single crystal X‐ray analysis. These studies revealed non‐covalent interactions that are the first‐of‐their‐kind including a unique iodine‐oxygen interaction between cubane units. These supramolecular architectures indicate the possibility to mimic a protein structure due to the sp3 rigid scaffolds (BCP or cubane) that exhibit the essential conformational space for protein function while simultaneously providing amide bonds for molecular recognition.

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Synthese von Bicyclo[1.1.1]pentan‐Bioisosteren von internen Alkinen und para‐disubstituierten Benzolen unter Verwendung von [1.1.1]Propellan

et al. 2017

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Wirb erichten über ein allgemeines Syntheseverfahren fürarylierte Bicyclo[1.1.1]pentane durch die Öffnung von [1.1.1]Propellan mit verschiedenen Arylmagnesiumhalogeniden. Nach Transmetallierung mit ZnCl 2 und einer Negishi-Kreuzkupplung mit Heteroaryl-oder Arylhalogeniden, werden diarylierte Bicyclo[1.1.1]pentane erhalten, die als Bioisostere von internen Alkinen betrachtet werden kçnnen.Bioisostere von Tazaroten und 2-Methyl-6-(phenylethinyl)pyridin, einem Antagonisten des metabotropen Glutamat-Rezeptors 5( mGluR5), wurden hergestellt und deren physikochemischen Eigenschaften ausgewertet.

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Propellane: von chemischen Kuriositäten zu “explosiven” Materialen und Naturstoffen

Cited by 35 publications

References 353 publications

Rhodium(III)‐Catalyzed Divergent C−H Functionalization of N‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts

Rhodium(III)‐Catalyzed Divergent C−H Functionalization of N‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts

Bridging and Conformational Control of Porphyrin Units through Non‐Traditional Rigid Scaffolds

Synthese von Bicyclo[1.1.1]pentan‐Bioisosteren von internen Alkinen und para‐disubstituierten Benzolen unter Verwendung von [1.1.1]Propellan

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