ChemInform Abstract: The Conversion of Alkoxysilanes in Fluorosulfonic Acid.

Kubasheva, I. A.; Musavirov, R. S.; Nedogrei, E. P.; Akhmatdinov, R.T.; Кантор, Е. А.; Rakhmankulov, D. L.

doi:10.1002/chin.198632217

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“…In analogy to the carbenium ion formation, Olah and co-workers attempted the generation of silylium ions in superacidic media from alkoxysilanes (Scheme A, with X = OR). − Using magic acid (HSO 3 F·SbF 5 ), the protonation of alkoxysilanes such as trimethylmethoxysilane was indeed detected by low temperature NMR spectroscopy, but the corresponding silyl fluoride was obtained as the final product ( 8 → 9 , Scheme , top). The same outcome is observed when alkoxy- as well as chlorosilanes (Scheme A, with X = Cl) are exposed to hydrogen fluoride , or fluorosulfonic acid alone. Likewise, the treatment of chlorosilanes with triflic acid − results in quenching of the incipient silyl cation by the triflate anion ( 10 → 11 , Scheme , bottom).…”

Section: Synthesis Of Carbenium and Silylium Ions By Protonation With...supporting

confidence: 55%

The Power of the Proton: From Superacidic Media to Superelectrophile Catalysis

Klare

Oestreich

2021

J. Am. Chem. Soc.

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Superacidic media became famous in connection with carbocations. Yet not all reactive intermediates can be generated, characterized, and eventually isolated from these Brønsted acid/Lewis acid cocktails. The counteranion, that is the conjugate base, in these systems is often too nucleophilic and/or engages in redox chemistry with the newly formed cation. The Brønsted acidity, especially superacidity, is in fact often not even crucial unless protonation of extremely weak bases needs to be achieved. Instead, it is the chemical robustness of the aforementioned counteranion that determines the success of the protolysis. The advent of molecular Brønsted superacids derived from weakly coordinating, redox-inactive counteranions that do withstand the enormous reactivity of superelectrophiles such as silicon cations completely changed the whole field. This Perspective summarizes general aspects of medium and molecular Brønsted acidity and shows how applications of molecular Brønsted superacids have advanced from stoichiometric reactions to catalytic processes involving protons and in situ generated superelectrophiles.

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Section: Synthesis Of Carbenium and Silylium Ions By Protonation With...supporting

confidence: 55%

The Power of the Proton: From Superacidic Media to Superelectrophile Catalysis

Klare

Oestreich

2021

J. Am. Chem. Soc.

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“…Kudasheva et al. demonstrated the synthesis of 2‐methylpropane‐1,2‐diyl difluorosulfate ( 60 ) through the reaction of 2‐methylpropane‐1,2‐diol ( 59 ) with fluorosulfonic acid (Scheme ) …”

Section: Synthesis Of Fluorosulfatesmentioning

confidence: 99%

Synthesis and Chemical Transformations of Fluorosulfates

Lekkala

Leng

et al. 2018

Asian J Org Chem

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Fluorosulfates are readilya vailablee lectrophiles that can be prepared from the reactions of phenol or alcohol derivatives with sulfuryl fluoride, fluorosulfonic acid, sulfuryl chloridef luoride, and fluorosulfonic anhydride. This Focus Review coversm ost of the synthetic strategies that have been reported for the construction of fluorosulfates,a s well as their application as versatile buildingb locks in av ariety of synthetic transformations, such as catalyzed amination, cross-coupling, sulfur(VI) fluoridee xchange, carbonylation, hydrolysis, alcoholysis,a nd as alternatives to organic halidesort riflates in organic chemistry.Scheme79. Synthesis of g-pyrone by using fluorosulfate 34.Scheme80. Reactions of fluorosulfatesw ith nucleophilicreagents.Scheme81. Synthesis of the desired allenefrom fluorosulfate 68. Scheme82. Preparation of benzenef rom phenyl fluorosulfate (110).Scheme83. Synthesis of compound 170 from fluorosulfate 169.

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ChemInform Abstract: The Conversion of Alkoxysilanes in Fluorosulfonic Acid.

Cited by 2 publications

References 0 publications

The Power of the Proton: From Superacidic Media to Superelectrophile Catalysis

The Power of the Proton: From Superacidic Media to Superelectrophile Catalysis

Synthesis and Chemical Transformations of Fluorosulfates

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