Über Aromatische Sulfofluoride

Steinkopf, Wilhelm

doi:10.1002/prac.19271170101

Cited by 83 publications

(58 citation statements)

References 17 publications

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“…As shown by entries 16-20 in Table V, the correlation between EI,,(RED) and up for series I1 is good at pH 8.0, slightly better at pH 2.2 (Figure a), 4.0, and 6.0, and excellent at pH 9.2. The least significant correlations between E1/,(RED) and u for both series I and I1 occur at pH 6.0 and 8.0.…”

Section: -Substituted 2-nitrophenols (11) With Substituentmentioning

confidence: 73%

Relationships between structure, polarography, and electronic spectra of 4- and 5-substituted 2-nitrophenols

Rodriguez¹,

Meyers²,

Hancock³

1970

J. Org. Chem.

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and the tendency of the lines to broaden at lower temperatures, we believe more realistic probable limits of error for AG+ and AH * are Et2 kcal/mol with a reasonable probability for substantial error in the value of AX*.series of measurements including those illustrated in Figure 2 Registry ~~~-4 , 24299-67-0; 5, 24299-68-1 6 , were AG* = 16.4 0.2 kcal/mol; AH* = 14.8 =! = 0.2 kcal/mol; A S * = -5.4 k 0.5 eu. Because of the relatively 24299-69-2; 7a1 24299-70-5; 7bi 24299-71-6; 8a, small separation of lines (3.5 Ha in the low-temperature limit)Polarographic oxidation potential, Ei/,(OX), and reduction potentials, Ei/,(RED), for a series of 4-and 5-substituted 2-nitrophenols have been measured in aqueous ethanol (10%) solutions buffered at pH 2.2, 4.0, 6.0, 8.0, and 9.2. Although both series appear to give polarographic waves characteristic of irreversible reactions, good correlations of Ei/,(OX) and Ei/,(RED) with the appropriate substituent constant, urn, up, or gpfl were obtained. Usually, the correlations that involved Ei/,(RED) were most satisfactory at low pH, while those that involved Ei/,(OX) were best at high pH. The correlation of the frequency of the longest wavelength maximum observed in the electronic spectrum with Ei/,(OX) or [Ei/,(OX) -Ei/,(RED)] WRS examined and found to be good for the 4-substituted compounds and poor for the 5-substituted ones. For the most widely divergent data, an attempt to explain the discrepancies has been made, but the investigation of other series would be desirable. (6) L. P . Hammett, "Physical The rates of spontaneous hydrolyses of substituted benzenesulfonyl fluorides in dioxane-water (40 : 60 v/v)

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Section: -Substituted 2-nitrophenols (11) With Substituentmentioning

confidence: 73%

Relationships between structure, polarography, and electronic spectra of 4- and 5-substituted 2-nitrophenols

Rodriguez¹,

Meyers²,

Hancock³

1970

J. Org. Chem.

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“…It was found that the best results were obtained when the reaction was performed in the presence of Pd(PPh 3 ) 2 Cl 2 and K 2 CO 3 in refluxing dioxane. Further optimization of the reaction conditions showed that switching to less-coordinating THF, as well as using Pd(dppf ) 2 Cl 2 as a catalyst and Na 3 PO 4 as a base allows for the preparation of the target cyclopropyl derivatives 37d-42d (Table 2, Entries 4,8,12,16,20,24). In this case, the products of double substitution 43 (39 % yield) and 44 (46 % yield) were formed under the standard conditions (Scheme 10).…”

Section: Resultsmentioning

confidence: 99%

“…• electrophilic substitution using fluorosulfonic acid; [23,24] • reaction of sulfonyl chlorides with fluorine anion source (KHF 2 , [5] KF, [25] TBAF, [26] NH 4 F, [27,28] or [ 18 F]KF -2.2.2-cryptand, [5,26] ); • oxidative chlorination of thiols, [29][30][31][32][33][34] sulfides [35,36] (Cl 2 , Na-ClO, NCS), followed by in situ nucleophilic substitution by fluorine anion (KHF 2 or BnNMe 3 + F -); • electrophilic fluorination of sulfinates or sulfonyl hydrazides. [37] A recently developed modification of this approach relies on in situ generation of sulfinate via palladium-catalyzed reaction of the corresponding aryl halides with DABSO, followed by oxidation with Selectfluor or NFSI; [38,39] • cycloaddition and heterocyclization reactions.…”

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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“…Although sulfonyl fluorides (SFs; Figure ) can be traced back 100 years in Germany for applications in dyes their application has been revitalized as sulfur(VI) fluoride exchange (SuFEx) reagents by Sharpless and co‐workers . These exchange reactions were reviewed and may be emerging as the next click reaction in chemical biology.…”

Section: Applications Of Affinity Labelingmentioning

confidence: 99%

“…Although sulfonyl fluorides (SFs;F igure 4) can be traced back 100 years in Germany for applications in dyes [21] their application has been revitalized as sulfur(VI) fluoride exchange (SuFEx) reagents by Sharpless and co-workers. [22] These exchange reactions were reviewed [23] and may be emerging as the next click reaction in chemical biology.T he SuFEx reaction includes several important reagent types-SFs,s ulfonimidoyl fluorides,f luorosulfates,a nd sulfamoyl fluoride-which show specific reactivity to several amino acids (e.g.T yr, Ser,T hr, His,L ys,and Cys).…”

Section: Sulfur(vi) Fluoride Exchange (Sufex) Reactionmentioning

confidence: 99%

The Application of Fluorine‐Containing Reagents in Structural Proteomics

2020

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Structural proteomics refers to large‐scale mapping of protein structures in order to understand the relationship between protein sequence, structure, and function. Chemical labeling, in combination with mass‐spectrometry (MS) analysis, have emerged as powerful tools to enable a broad range of biological applications in structural proteomics. The key to success is a biocompatible reagent that modifies a protein without affecting its high‐order structure. Fluorine, well‐known to exert profound effects on the physical and chemical properties of reagents, should have an impact on structural proteomics. In this Minireview, we describe several fluorine‐containing reagents that can be applied in structural proteomics. We organize their applications around four MS‐based techniques: a) affinity labeling, b) activity‐based protein profiling (ABPP), c) protein footprinting, and d) protein cross‐linking. Our aim is to provide an overview of the research, development, and application of fluorine‐containing reagents in protein structural studies.

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Über Aromatische Sulfofluoride

Cited by 83 publications

References 17 publications

Relationships between structure, polarography, and electronic spectra of 4- and 5-substituted 2-nitrophenols

Relationships between structure, polarography, and electronic spectra of 4- and 5-substituted 2-nitrophenols

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

The Application of Fluorine‐Containing Reagents in Structural Proteomics

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Über Aromatische Sulfofluoride

Cited by 83 publications

References 17 publications

Relationships between structure, polarography, and electronic spectra of 4- and 5-substituted 2-nitrophenols

Relationships between structure, polarography, and electronic spectra of 4- and 5-substituted 2-nitrophenols

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

The Application of Fluorine‐Containing Reagents in Structural Proteomics

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