Iterative Synthesen: das Tor zu neuen Automationsprotokollen

Hartwig, Jan; Kirschning, Andreas

doi:10.1002/ange.201504615

Angewandte Chemie

2015

DOI: 10.1002/ange.201504615

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Iterative Synthesen: das Tor zu neuen Automationsprotokollen

Jan Hartwig

Andreas Kirschning

Abstract: Automation steht wieder auf der Tagesordnung! Der erste automatisierte, iterative C‐C‐Kupplungsprozess nutzt die beiden Gesichter von MIDA‐Boronaten. Es werden die Möglichkeiten und Herausforderungen offenbart, wie iterative Synthesen mit komplexen, bifunktionalisierten Bausteinen unter Nutzung von „Liquid‐Handling”︁‐Systemen sogar Naturstoffsynhesen möglich machen.

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Cited by 5 publications

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“…Conceptually, modularity and iteration are common concepts that occur in nature and manifest themselves in polypeptides, oligonucleotides, and oligosaccharides as well as in secondary metabolites such as terpenes and polyketides . Strategically, iteration is still in its infancy in many areas of synthesis.…”

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Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

Kuhwald

Kirschning

2021

Org. Lett.

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The Matteson reaction is ideally suited for flow chemistry since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative workup. The new terpene alcohols are validated with respect to their olfactoric properties.

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Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

Kuhwald

Kirschning

2021

Org. Lett.

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Die molekulare industrielle Revolution: zur automatisierten Synthese organischer Verbindungen

Trobe

Burke

2018

Angewandte Chemie

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Derzeitkündigt sichein Wandel von der manuellen Synthese spezifischer Moleküle,die über individuell angepasste Routen verläuft, hin zu automatisch zusammenfügten Verbindungen unterschiedlichster Klassen mit nur einem Knopfdruckan. Die Entwicklung einer Maschine fürdie Herstellung unterschiedlichsterorganischer Moleküle je nachBedarf ist eine komplexe Aufgabe,e ss ind aber bereits bedeutende Fortschritte auf Basis von zwei komplementären Ansätzen zu verzeichnen:1 )Automatisierung individueller Routen fürdie Synthese diverser Verbindungen, wobei viele unterschiedliche Reaktionstypen und spezifische Reagentien genutzt werden kçnnen, und 2) Automatisierung einer generellen Plattform, die die Herstellung unterschiedlicher Verbindungen ausgehend von diversen Bausteinen, die mit derselben Kupplungsreaktion verknüpft werden, ermçglicht. Fortschritte in diesen Bereichen bieten die Mçglichkeit, Synthese-Engpässe zu vermeiden und den Fokus molekularer Innovation auf die Entwicklung neuer Methoden zu lenken und so eine "molekulare industrielle Revolution" zu beschleunigen.

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Modular and Selective Arylation of Aryl Germanes (C−GeEt₃) over C−Bpin, C−SiR₃ and Halogens Enabled by Light‐Activated Gold Catalysis

et al. 2020

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Selective Csp2 –Csp2 couplings are powerful strategies for the rapid and programmable construction of bi‐ or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd‐catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C−BPin, C−SiMe3, C−I, C−Br, C−Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C−Ge with aryl diazonium salts. Contrary to previous light‐/gold‐catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron‐rich, electron‐poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron‐poor Ar–N2+ salts are readily activated by gold under blue‐light irradiation, there is a competing dissociative deactivation pathway for excited electron‐rich Ar–N2+, which requires an alternative photo‐redox approach to enable productive couplings.

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Iterative Synthesen: das Tor zu neuen Automationsprotokollen

Cited by 5 publications

References 10 publications

Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

Die molekulare industrielle Revolution: zur automatisierten Synthese organischer Verbindungen

Modular and Selective Arylation of Aryl Germanes (C−GeEt₃) over C−Bpin, C−SiR₃ and Halogens Enabled by Light‐Activated Gold Catalysis

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Iterative Synthesen: das Tor zu neuen Automationsprotokollen

Cited by 5 publications

References 10 publications

Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

Die molekulare industrielle Revolution: zur automatisierten Synthese organischer Verbindungen

Modular and Selective Arylation of Aryl Germanes (C−GeEt3) over C−Bpin, C−SiR3 and Halogens Enabled by Light‐Activated Gold Catalysis

Contact Info

Product

Resources

About

Modular and Selective Arylation of Aryl Germanes (C−GeEt₃) over C−Bpin, C−SiR₃ and Halogens Enabled by Light‐Activated Gold Catalysis