Über Aromatische Sulfofluoride. II. Mitteilung

Steinkopf, Wilhelm; Jaeger, Paul T.

doi:10.1002/prac.19301280104

Cited by 45 publications

(18 citation statements)

References 5 publications

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“…Thus far, various inorganic and organic fluorination reagents have been employed for this purpose:H F, [19] NaF, [20] KF, [21] KHF 2 , [22] CsF, [23] ZnF 2 , [24] HBF 4 , [25] Na 2 SiF 6 , [26] Bu 4 NF (TBAF), [27] SbF 3 , [28] KSO 2 F, [29] SeF 4 , [30] F 2 (aerosol), [31] BrF 3 , [32] XeF 2 , [33] SF 4 , [34] R 2 NÀSF 3 (DAST, [35] morpholinosulfur trifluoride, [36] and Deoxo-Fluor [37] ), (R 2 N=SF 2 )BF 4 (XtalFluor), [38] ArSF 3 (Fluolead), [39] (Me 4 N)SCF 3 , [40] cyanuric fluoride, [6,41] 2-fluoropyridinium salts, [42] fluoro formamidinium salts (TFFH and BTFFH), [43] perfluoroalkylamines (e.g.,Y arovenkosreagent and Ishikawasr eagent), [44] PhCOF, [45] and other Fs ources (Scheme 4B). [46] Among these synthetic methods,the following fluorinating reagents are especially practical and useful: HF, [19] DAST, [35] Deoxo-Fluor [37] (Me 4 N)SCF 3 , [40] and cyanuric fluoride. [6,41] Va rious types of acyl fluorides are effectively and easily obtainable from the corresponding carboxylic acids with these reagents,r egardless of their carbon framework or their functional groups.…”

Section: Formation Of Acyl Fluoridesmentioning

confidence: 99%

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: 99%

Acyl Fluorides in Late‐Transition‐Metal Catalysis

2019

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“…), [44] PhCOF [45] und weitere F-Quellen (Schema 4B). [46] Unter diesen Synthesemethoden gelten folgende Fluorierungsreagenzien als besonders praktikabel und nützlich:HF, [19] DAST, [35] Deoxo-Fluor [37] (Me 4 N)SCF 3 [40] und Cyanurfluorid. [6,41] Verschiedene Arten von Carbonsäurefluoriden sind aus den jeweiligen Carbonsäuren mithilfe dieser Reagenzien effizient und leicht zugänglich, unabhängig von deren Kohlenstoffgerüst oder funktionellen Gruppen.…”

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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“…[40][41][42] It should be noted that to the best of our knowledge, heteroaromatic sulfonyl fluorides bearing a bromine or iodine atom suitable for metal-catalyzed C-C coupling reactions were not described in the literature to date (although some representa-tives of SO 2 F-substituted hetaryl chlorides were known, see Scheme 1). [43] Nevertheless, first examples of the palladium-catalyzed cross-coupling (i.e. In particular, aryl halides 8 were introduced into the Ullmann reaction as early as in 1930 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

“…In particular, aryl halides 8 were introduced into the Ullmann reaction as early as in 1930 (Scheme 2). [43] Nevertheless, first examples of the palladium-catalyzed cross-coupling (i.e. the Suzuki reaction) of bromo/iodo derivatives of benzenesulfonyl fluorides 9 were reported only in 2016.…”

Section: Introductionmentioning

confidence: 99%

Hetaryl Bromides Bearing the SO₂F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

et al. 2018

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Synthesis of novel five‐ and six‐membered heteroaromatic sulfonyl fluorides bearing bromine atom at various positions of the heterocyclic ring is described. The synthetic utility of these compounds is demonstrated by the Suzuki, Stille, and Negishi cross‐coupling reactions, which proceeded chemoselectively at the aryl bromide moiety with 69–98 % yields. The tolerance of the SO2F group towards the coupling reaction conditions was confirmed in most of the experiments. The proposed method was efficient for either sp2–sp2 or sp2–sp3 C–C couplings. The developed procedure provides rapid access to various substituted heterocyclic sulfonyl fluorides.

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Über Aromatische Sulfofluoride. II. Mitteilung

Cited by 45 publications

References 5 publications

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Carbonsäurefluoride in der Katalyse durch späte Übergangsmetalle

Hetaryl Bromides Bearing the SO₂F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

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Über Aromatische Sulfofluoride. II. Mitteilung

Cited by 45 publications

References 5 publications

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Carbonsäurefluoride in der Katalyse durch späte Übergangsmetalle

Hetaryl Bromides Bearing the SO2F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

Contact Info

Product

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Hetaryl Bromides Bearing the SO₂F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions