Preparation and Synthetic Applications of Aryl Tetraflates (ArOSO2CF2CF2H)

Rostovtsev, Vsevolod V.; Bryman, Lois M.; Junk, Christopher P.; Harmer, Mark A.; Carcani, Liane G.

doi:10.1021/jo701630a

Cited by 10 publications

(5 citation statements)

References 23 publications

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“…The corresponding triflate provided 91 with inferior efficacy. The lower homologues of nonaflates, tetraflates (C 2 F 4 HSO 2 ‐OR) were also applied to Suzuki and Heck couplings as well as Pd‐catalyzed amination reactions 82…”

Section: Miscellaneous Reactions Including Other Perfluorosulfonylamentioning

confidence: 99%

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

2009

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How much fluoride is good for a strong electron-withdrawing effect? In this review we summarize recent results on the use of perfluoroalkanesulfonates, in particular of the cost effective nonafluorobutanesulfonates (nonaflates), in transition metal-catalyzed reactions and a few other typical transformations. During the last decade many advantages over the commonly used triflates have been discovered. The generation of alkenyl and (het)aryl nonaflates and their applications in metal-catalyzed processes such as Heck, Suzuki, Sonogashira, Stille, and Negishi couplings or amination reactions are described. Although far from a systematic investigation, all the presented results clearly demonstrate the many advantages of nonaflates and of similar higher fluorinated sulfonates in laboratory and industrial scale organic synthesis.

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Section: Miscellaneous Reactions Including Other Perfluorosulfonylamentioning

confidence: 99%

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

2009

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“…To establish another efficient method for the production of fluorophores 1 by Buchwald−Hartwig amination, various ligands were used in the coupling of bistriflate 12b with N -naphthyl- N -phenylamine. ,, Table presents the Buchwald−Hartwig amination of the bistriflate 12b with N -naphthyl- N -phenylamine examined in the presence of 3 mol % of Pd 2 (dba) 3 , 9 mol % of ligand, and 2 equiv of t BuONa in toluene solution. The amination with ligands P( t Bu) 3 , − , DPPF, and BINAP is inefficient.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photophysical Properties of Pyrrole/Polycyclic Aromatic Units Hybrid Fluorophores

Tsai

Lee

et al. 2010

J. Org. Chem.

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A series of pyrrole/polycyclic aromatic unit hybrid fluorophores was developed by a two-stage synthetic strategy. Their central aryl-substituted pyrrole cores were constructed by a Paal-Knorr pyrrole synthesis reaction. The reaction conditions and mechanism are also discussed in detail. End-capping triflate onto the central pyrrole core enables the core to incorporate various polycyclic aromatic units. The Buchwald-Hartwig amination reaction and the Suzuki-Miyaura cross-coupling reaction were adopted to incorporate the triflate end-capping pyrrole with N-phenylnaphthalen-1-amine and various polycyclic aromatic units to form the hybrid fluorophores. The photophysical properties and thermal properties of the fluorophores were characterized. Most of the pyrrole fluorophores emitted blue light and exhibited high quantum efficiency. The fluorescence properties of these pyrrole fluorophores were induced by manipulating the surrounding polycyclic aromatic units. When the central pyrrole core was incorporated with amino or naphthalene moieties, the fluorescence efficiency and thermal stability of fluorophores 1 and 2 were low (phi(f) < 0.35, T(g) <140 degrees C). Rigid and highly fluorescent moieties (such as pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, and spirofluorenyl groups) were grafted onto the pyrrole. Fluorophores 3-6 had high fluorescence efficiency (phi(f) > 0.99) and stable glassy morphology (the T(g) value of the fluorophore 6 was as high as 220 degrees C). Results of this study demonstrate that the sterically induced fluorescence of crowded pyrrole and the fluorescent polycyclic aromatic units significantly affect the emission properties of the hybrid fluorophores.

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“…The synthesis of TFESA and HFPSA has recently been described. 2 For TFESA: 19 F NMR (CD 3 OD) d -125.2 (dt, 3 J FH = 6 Hz, 3 J FF = 8 Hz, 2F); -137.6 (dt, 2 J FH = 53 Hz, 2F). 1 H NMR (CD 3 OD) d 6.3 (tt, 3 J FH = 6 Hz, 2 J FH = 53 Hz, 1H).…”

Section: Methodsmentioning

confidence: 99%

“…2 For TFESA: 19 F NMR (CD 3 OD) d -125.2 (dt, 3 J FH = 6 Hz, 3 J FF = 8 Hz, 2F); -137.6 (dt, 2 J FH = 53 Hz, 2F). 1 H NMR (CD 3 OD) d 6.3 (tt, 3 J FH = 6 Hz, 2 J FH = 53 Hz, 1H). For HFPSA: 19 The ionic liquids were synthesized from the respective halides of the cations and the corresponding potassium sulfonate salt of the acid.…”

Section: Methodsmentioning

confidence: 99%

“…In this paper, we will expand upon our earlier work, namely the use of new Brønsted superacidic catalysts for a number of acid catalyzed reactions of industrial importance. 2, 3 Traditional homogeneous acids, such as hydrofluoric (exceptionally hazardous) and sulfuric acids have a number of drawbacks in industrial processes including the generation of large amounts of waste associated with product separation. Replacement of these acids with highly active catalysts (such as superacids) that can be recycled and easily separated has the potential to reduce waste, reduce energy needs, cut down the process time, and make the overall process safer and more economical.…”

Section: Introductionmentioning

confidence: 99%

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