Frank Glorius

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N‐Heterocyclic Olefins on a Silicon Surface

Mowpriya Das, Conor Hogan, Robert Zielinski, Milan Kubicki, more

Angewandte Chemie International Edition > 62 > 50 > n/a - n/a

The adsorption of N‐heterocyclic olefins (NHOs) on silicon is investigated in a combined scanning tunneling microscopy, X‐ray photoelectron spectroscopy, and density functional theory study. We find that both of the studied NHOs bind covalently, with ylidic character, to the silicon adatoms of the substrate and exhibit good thermal stability. The adsorption geometry strongly depends on the N‐substituents:...

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N‐Heterocyclic Olefins on a Silicon Surface

Mowpriya Das, Conor Hogan, Robert Zielinski, Milan Kubicki, more

Angewandte Chemie > 135 > 50 > n/a - n/a

The adsorption of N‐heterocyclic olefins (NHOs) on silicon is investigated in a combined scanning tunneling microscopy, X‐ray photoelectron spectroscopy, and density functional theory study. We find that both of the studied NHOs bind covalently, with ylidic character, to the silicon adatoms of the substrate and exhibit good thermal stability. The adsorption geometry strongly depends on the N‐substituents:...

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Surface Modification of ITO with N‐Heterocyclic Carbene Precursors Results in Electron Selective Contacts in Organic Photovoltaic Devices

Mowpriya Das, Markus Kohlstädt, Maria Enders, Stephan Burger, more

Chemistry – A European Journal > 29 > 60 > n/a - n/a

Surface modification of indium tin oxide (ITO) electrodes with organic molecules is known to tune their work function which results in higher charge carrier selectivity in corresponding organic electronic devices and hence influences the performance of organic solar cells. In recent years, N‐heterocyclic carbenes (NHCs) have also been proven to be capable to modify the work function of metals and...

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Catalytic Formal [2π+2σ] Cycloaddition of Aldehydes with Bicyclobutanes: Expedient Access to Polysubstituted 2‐Oxabicyclo[2.1.1]hexanes

Yujie Liang, Fritz Paulus, Constantin G. Daniliuc, Frank Glorius

Angewandte Chemie International Edition > 62 > 34 > n/a - n/a

Synthesis of bicyclic scaffolds has attracted tremendous attention because they are playing an important role as saturated bioisosteres of benzenoids in modern drug discovery. Here, we report a BF₃‐catalyzed [2π+2σ] cycloaddition of aldehydes with bicyclo[1.1.0]butanes (BCBs) to access polysubstituted 2‐oxabicyclo[2.1.1]hexanes. A new kind of BCB containing an acyl pyrazole group was invented, which...

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Katalytische formale [2π+2σ]‐Cycloaddition von Aldehyden mit Bicyclobutanen: Zweckmäßiger Zugang zu polysubstituierten 2‐Oxabicyclo[2.1.1]hexanen

Yujie Liang, Fritz Paulus, Constantin G. Daniliuc, Frank Glorius

Angewandte Chemie > 135 > 34 > n/a - n/a

Die Synthese von bicyclischen Gerüsten hat jüngst großes Interesse erregt, da diese als gesättigte Bioisostere von Benzoiden eine wichtige Rolle in der modernen Wirkstoffforschung spielen. In dieser Arbeit berichten wir über eine BF₃‐katalysierte [2π+2σ]‐Cycloaddition von Aldehyden mit Bicyclo[1.1.0]butanen (BCBs), um polysubstituierte 2‐Oxabicyclo[2.1.1]hexane zu synthetisieren. Zu diesem Zweck wurde...

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Stereochemical Editing

Guangying Tan, Frank Glorius

Angewandte Chemie > 135 > 11 > n/a - n/a

Stereochemical editing has recently risen to prominence, allowing the direct editing of organic molecules with stereocenter(s) to adjust their relative stereochemistry at a late‐stage. Several seminal light‐driven stereochemical editing reactions such as deracemization and epimerization have been successively developed. Recently, Wendlandt and co‐workers reported a versatile photochemical epimerization...

article

Stereochemical Editing

Guangying Tan, Frank Glorius

Angewandte Chemie International Edition > 62 > 11 > n/a - n/a

Stereochemical editing has recently risen to prominence, allowing the direct editing of organic molecules with stereocenter(s) to adjust their relative stereochemistry at a late‐stage. Several seminal light‐driven stereochemical editing reactions such as deracemization and epimerization have been successively developed. Recently, Wendlandt and co‐workers reported a versatile photochemical epimerization...

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Chrom/Photoredox‐dualkatalysierte Synthese von α‐benzylischen Alkoholen, Isochromanonen, 1,2‐Oxyalkoholen und 1,2‐Thioalkoholen

Subhabrata Dutta, Johannes E. Erchinger, Felix Schäfers, Ankita Das, more

Angewandte Chemie > 134 > 49 > n/a - n/a

In diesem Artikel wird eine allgemeine Cr/Photoredox‐katalysierte Synthesestrategie für den Zugang zu α‐benzylischen Alkoholen, Isochromanonen, Oxyalkoholen und Thioalkoholen vorgestellt. Da die Alkylierung von Aldehyden eine wichtige C−C‐Bindungsbildungsreaktion darstellt, ermöglicht die Entwicklung kompetenter katalytischer Systeme die Darstellung dekorierter Alkoholmotive. Angesichts der Herausforderungen,...

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Chromium/Photoredox Dual Catalyzed Synthesis of α‐Benzylic Alcohols, Isochromanones, 1,2‐Oxy Alcohols and 1,2‐Thio Alcohols

Subhabrata Dutta, Johannes E. Erchinger, Felix Schäfers, Ankita Das, more

Angewandte Chemie International Edition > 61 > 49 > n/a - n/a

Herein, a Cr/Photoredox‐catalyzed general synthetic strategy to access α‐benzylic alcohols, isochromanones, oxy alcohols and thio alcohols is unveiled. Alkylation of aldehydes being a crucial C−C bond forming reaction, designing competent catalytic systems would render an attractive and decorated set of diverse alcohol motifs. Considering the challenges associated with classical organometallic chemistry,...

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Front Cover Picture: Special Issue Dedicated to Andreas Pfaltz (Adv. Synth. Catal. 19/2022)

Frank Glorius, Qi‐Lin Zhou

Advanced Synthesis & Catalysis > 364 > 19 > 3321 - 3321

The front cover picture shows examples of work developed by Professor Andreas Pfaltz, to whom this special issue of Advanced Synthesis & Catalysis is dedicated. For details see the commentary by the Issue Editors, Frank Glorius and Qi‐Lin Zhou (F. Glorius, Q.‐L. Zhou, Adv. Synth. Catal. 2022, 364, 3322–3323; DOI: 10.1002/adsc.202200973).

article

Special Issue Dedicated to Andreas Pfaltz

Frank Glorius, Qi‐Lin Zhou

Advanced Synthesis & Catalysis > 364 > 19 > 3322 - 3323

No Abstract

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Synthesis of Saturated N‐Heterocycles via a Catalytic Hydrogenation Cascade

Tobias Wagener, Marco Pierau, Arne Heusler, Frank Glorius

Advanced Synthesis & Catalysis > 364 > 19 > 3366 - 3371

Saturated N‐heterocycles are prominent motifs found in various natural products and pharmaceuticals. Despite the increasing interest in this class of compounds, the synthesis of saturated bicyclic azacycles requires tedious multi‐step syntheses. Herein, we present a one‐pot protocol for the synthesis of octahydroindoles, decahydroquinolines, and octahydroindolizines through a cascade reaction.

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Zugang zu neuem 3D chemischen Raum: cis‐selektive Aromatenhydrierung zur Synthese gesättigter cyclischer Boronsäuren

Akash Kaithal, Tobias Wagener, Peter Bellotti, Constantin G. Daniliuc, more

Angewandte Chemie > 134 > 32 > n/a - n/a

Eine neue Klasse gesättigter, zyklischer Borverbindungen wurde mit Hilfe einer Aromatenhydrierung synthetisiert. Berichtet wird über die cis‐selektive Hydrierung von leicht zugänglichen und biologisch bedeutsamen Verbindungen, darunter Benzoxaborole, Benzoxaborinine und Benzoxaboripine. Unter den verschiedenen getesteten Katalysatoren wurde mit dem cyclischen Rhodium(alkyl)(amino)carben [Rh‐CAAC]...

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Access to Unexplored 3D Chemical Space: cis‐Selective Arene Hydrogenation for the Synthesis of Saturated Cyclic Boronic Acids

Akash Kaithal, Tobias Wagener, Peter Bellotti, Constantin G. Daniliuc, more

Angewandte Chemie International Edition > 61 > 32 > n/a - n/a

A new class of saturated boron‐incorporated cyclic molecules has been synthesized employing an arene‐hydrogenation methodology. cis‐Selective hydrogenation of easily accessible, and biologically important molecules comprising benzoxaborole, benzoxaborinin, and benzoxaboripin derivatives is reported. Among the various catalysts tested, rhodium cyclic(alkyl)(amino)carbene [Rh‐CAAC] (1) pre‐catalyst...

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Wachstum von N‐heterocyclischen Carbenen auf Cu(100) und Cu(111): von einzelnen Molekülen bis hin zu Inseln mit magischen Zahlen

Juan J. Navarro, Mowpriya Das, Sergio Tosoni, Felix Landwehr, more

Angewandte Chemie > 134 > 30 > n/a - n/a

N‐Heterocyclische Carbene (NHCs) haben ausgezeichnete Eigenschaften als Bausteine von selbstorganisierten Monoschichten (SAMs). Bevor diese Moleküle in technologischen Anwendungen zum Einsatz kommen können, ist als grundlegender Schritt der Einfluss des Substrates auf molekulare Anordnungen zu verstehen. Hier untersuchen wir die molekulare Anordnung eines Modell‐NHC auf Cu(100) und Cu(111). Während...

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Growth of N‐Heterocyclic Carbene Assemblies on Cu(100) and Cu(111): From Single Molecules to Magic‐Number Islands

Juan J. Navarro, Mowpriya Das, Sergio Tosoni, Felix Landwehr, more

Angewandte Chemie International Edition > 61 > 30 > n/a - n/a

N‐Heterocyclic carbenes (NHCs) have superior properties as building blocks of self‐assembled monolayers (SAMs). Understanding the influence of the substrate in the molecular arrangement is a fundamental step before employing these ligands in technological applications. Herein, we study the molecular arrangement of a model NHC on Cu(100) and Cu(111). While mostly disordered phases appear on Cu(100),...

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Maschinelles Lernen zur Vorhersage chemischer Reaktivität: Die Bedeutung “gescheiterter” Experimente

Felix Strieth‐Kalthoff, Frederik Sandfort, Marius Kühnemund, Felix R. Schäfer, more

Angewandte Chemie > 134 > 29 > n/a - n/a

Die quantitative Vorhersage der Ergebnisse chemischer Reaktionen ist eine zentrale Herausforderung in allen synthetischen Disziplinen. Während die darauf aufbauenden Optimierungsprobleme klassischerweise empirisch adressiert werden, birgt die datengestützte Modellierung ein enormes Potential, diese Prozesse zu beschleunigen. Für solche Vorhersagemodelle werden jedoch große Mengen hochwertiger Daten...

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Machine Learning for Chemical Reactivity: The Importance of Failed Experiments

Felix Strieth‐Kalthoff, Frederik Sandfort, Marius Kühnemund, Felix R. Schäfer, more

Angewandte Chemie International Edition > 61 > 29 > n/a - n/a

Assessing the outcomes of chemical reactions in a quantitative fashion has been a cornerstone across all synthetic disciplines. Classically approached through empirical optimization, data‐driven modelling bears an enormous potential to streamline this process. However, such predictive models require significant quantities of high‐quality data, the availability of which is limited: Main reasons for...

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Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

Jindong Ren, Matthias Freitag, Yuxiang Gao, Peter Bellotti, more

Angewandte Chemie International Edition > 61 > 13 > n/a - n/a

Self‐assembly of cyclohexyl cyclic (alkyl)(amino)carbenes (cyCAAC) can be realized and reversibly switched from a close‐packed trimer phase to a chainlike dimer phase, enabled by the ring‐flip of the cyclohexyl wingtip. Multiple methods including scanning tunneling microscopy (STM), X‐ray photoelectron spectroscopy (XPS) and density functional theory (DFT) calculations identified a distinct isomer...

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Reversible Selbstorganisation eines N‐heterocyclischen Carbens auf Metalloberflächen

Jindong Ren, Matthias Freitag, Yuxiang Gao, Peter Bellotti, more

Angewandte Chemie > 134 > 13 > n/a - n/a

Cyclohexyl(alkyl)(amino)carbene (cyCAAC) bilden selbstorganisierende Monolagen, die durch den Ring‐Flip der Cyclohexyl‐Seitengruppe reversibel von einer dicht gepackten Trimer‐Phase in eine kettenartige Dimer‐Phase umgeschaltet werden können. Mehrere Methoden, darunter Rastertunnelmikroskopie (STM), Röntgen‐Photoelektronenspektroskopie (XPS) und Dichtefunktionaltheorie (DFT)‐Berechnungen, identifizierten...

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Search results for: Frank Glorius

N‐Heterocyclic Olefins on a Silicon Surface

N‐Heterocyclic Olefins on a Silicon Surface

Surface Modification of ITO with N‐Heterocyclic Carbene Precursors Results in Electron Selective Contacts in Organic Photovoltaic Devices

Catalytic Formal [2π+2σ] Cycloaddition of Aldehydes with Bicyclobutanes: Expedient Access to Polysubstituted 2‐Oxabicyclo[2.1.1]hexanes

Katalytische formale [2π+2σ]‐Cycloaddition von Aldehyden mit Bicyclobutanen: Zweckmäßiger Zugang zu polysubstituierten 2‐Oxabicyclo[2.1.1]hexanen

Stereochemical Editing

Stereochemical Editing

Chrom/Photoredox‐dualkatalysierte Synthese von α‐benzylischen Alkoholen, Isochromanonen, 1,2‐Oxyalkoholen und 1,2‐Thioalkoholen

Chromium/Photoredox Dual Catalyzed Synthesis of α‐Benzylic Alcohols, Isochromanones, 1,2‐Oxy Alcohols and 1,2‐Thio Alcohols

Front Cover Picture: Special Issue Dedicated to Andreas Pfaltz (Adv. Synth. Catal. 19/2022)

Special Issue Dedicated to Andreas Pfaltz

Synthesis of Saturated N‐Heterocycles via a Catalytic Hydrogenation Cascade

Zugang zu neuem 3D chemischen Raum: cis‐selektive Aromatenhydrierung zur Synthese gesättigter cyclischer Boronsäuren

Access to Unexplored 3D Chemical Space: cis‐Selective Arene Hydrogenation for the Synthesis of Saturated Cyclic Boronic Acids

Wachstum von N‐heterocyclischen Carbenen auf Cu(100) und Cu(111): von einzelnen Molekülen bis hin zu Inseln mit magischen Zahlen

Growth of N‐Heterocyclic Carbene Assemblies on Cu(100) and Cu(111): From Single Molecules to Magic‐Number Islands

Maschinelles Lernen zur Vorhersage chemischer Reaktivität: Die Bedeutung “gescheiterter” Experimente

Machine Learning for Chemical Reactivity: The Importance of Failed Experiments

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

Reversible Selbstorganisation eines N‐heterocyclischen Carbens auf Metalloberflächen

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