High-throughput evaluation of in situ-generated cobalt(<scp>iii</scp>) catalysts for acyl fluoride synthesis

Lee, Graham M.; Clément, Roxanne; Baker, R. Tom

doi:10.1039/c7cy01519d

Cited by 21 publications

(25 citation statements)

References 26 publications

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“…In this report, numerous other cobalt complexes were prepared and screened for their catalytic activity towards acyl Cl/F exchange using a high‐throughput experimental approach . The authors identified CpCo(I) 2 (PPh 2 Me) as a highly active catalyst, and decided to use it for the synthesis of acyl fluorides given its practical handling and availability (Scheme ).…”

Section: Formation Of Acyl Fluoridesmentioning

confidence: 88%

Acyl Fluorides in Late‐Transition‐Metal Catalysis

2019

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In this Review, we summarize the current state of the art in late‐transition‐metal‐catalyzed reactions of acyl fluorides, covering both their synthesis and further transformations. In organic reactions, the relationship between stability and reactivity of the starting substrates is usually characterized by a trade‐off. Yet, acyl fluorides display a very good balance between these properties, which is mostly due to their moderate electrophilicity. Thus, acyl fluorides (RCOF) can be used as versatile building blocks in transition‐metal‐catalyzed reactions, for example, as an “RCO” source in acyl coupling reactions, as an “R” source in decarbonylative coupling reactions, and as an “F” source in fluorination reactions. Starting from the cleavage of the acyl C−F bond in acyl fluorides, various transformations are accessible, including C−C, C−H, C−B, and C−F bond‐forming reactions that are catalyzed by transition‐metal catalysts that contain the Group 9–11 metals Co, Rh, Ir, Ni, Pd, or Cu.

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Section: Formation Of Acyl Fluoridesmentioning

confidence: 88%

Acyl Fluorides in Late‐Transition‐Metal Catalysis

2019

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“…42 Shortly after, they screened 96 new cobalt(III) catalysts and evaluated their activity in the catalytic nucleophilic fluorination of benzoyl chloride (Scheme 23b). 43 After a highly active catalyst was identified CpCoI 2 (PPh 2 Me) (15b) and the optimized conditions determined, this procedure was successfully applied to a variety of acyl chlorides thus providing the corresponding acyl fluorides in excellent NMR yields (>80%).…”

Section: Cobalt-catalyzed Reactionsmentioning

confidence: 99%

Recent Advances in the Synthesis of Acyl Fluorides

Gonay¹,

Batisse²,

Paquin³

2020

Synthesis

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Acyl fluorides are valuable intermediates in organic synthesis. They are increasingly employed in peptide synthesis, in challenging esterification and amidation reactions or in transition-metal-catalyzed transformations. This review summarizes recent advances in their preparation.1 Introduction2 Nucleophilic Fluorination2.1 α-Fluoroamine Reagents2.2 Sulfur-Based Reagents2.3 Metal Catalysts2.4 Phosphorus-Based Reagents2.5 N,N′-Dicyclohexylcarbodiimide/HF·Pyridine2.6 Uranium Hexafluoride2.7 Bromine Trifluoride3 Radical Fluorination4 Conclusion

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“…Im Zuge dieses Berichts wurden zahlreiche weitere Cobaltkomplexe hergestellt und hinsichtlich ihrer katalytischen Aktivität im Acyl‐Cl/F‐Austausch mithilfe einer Hochdurchsatzmethode untersucht . Die Autoren identifizierten CpCo(I) 2 (PPh 2 Me) als sehr aktiven Katalysator und entschieden sich für dessen Verwendung in der Synthese von Carbonsäurefluoriden wegen seiner praktischen Handhabung und Verfügbarkeit (Schema ).…”

Section: Herstellung Von Carbonsäurefluoridenunclassified

Carbonsäurefluoride in der Katalyse durch späte Übergangsmetalle

Ogiwara

Sakai

2019

Angewandte Chemie

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In diesem Aufsatz fassen wir den aktuellen Forschungsstand bei durch späte Übergangsmetalle katalysierten Reaktionen von Carbonsäurefluoriden zusammen, inklusive deren Herstellung und Umsetzungen. In organischen Reaktionen muss oftmals ein Kompromiss zwischen Stabilität und Reaktivität der Startmaterialien gefunden werden. Carbonsäurefluoride weisen, hauptsächlich dank ihrer moderaten Elektrophilie, eine ausgezeichnete Balance zwischen diesen Eigenschaften auf. Daher können Carbonsäurefluoride (RCOFs) als vielseitige Bausteine in Übergangsmetall‐katalysierten Reaktionen verwendet werden, beispielsweise als “RCO”‐Quelle in Acylkupplungen, als “R”‐Quelle in decarbonylierenden Kupplungen und als “F”‐Quelle in Fluorierungen. Beginnend mit der Spaltung der C(Acyl)‐F‐Bindung in Carbonsäurefluoriden werden diverse, durch Übergangsmetallkatalysatoren auf Grundlage von Metallen der Gruppen 9–11 (wie Co, Rh, Ir, Ni, Pd oder Cu) vermittelte Transformationen zugänglich, einschließlich C‐C‐, C‐H‐, C‐B‐ und C‐F‐Bindungsknüpfungen.

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High-throughput evaluation of in situ-generated cobalt(iii) catalysts for acyl fluoride synthesis

Abstract: Using a high-throughput experimental procedure, a series of cobalt(iii) complexes of the general formula CpRCo(I)(X)(L) were prepared and screened for their activity towards the catalytic nucleophilic fluorination of benzoyl chloride.

Cited by 21 publications

References 26 publications

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Recent Advances in the Synthesis of Acyl Fluorides

Carbonsäurefluoride in der Katalyse durch späte Übergangsmetalle

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