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Search for "umpolung" in Full Text gives 51 result(s) in Beilstein Journal of Organic Chemistry.

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Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

Norio Shibata,
Andrej Matsnev and
Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

stability compared to the intermediates with Rf groups with more than one carbon atom. In 2006 Togni and co-workers reported a new family of hypervalent iodine compounds in which the CF3 group is bonded directly to the iodine atom. The overall synthetic protocol depends on a formal umpolung of the CF3 group

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Graphical Abstract

Scheme 1: Preparation of the first electrophilic trifluoromethylating reagent and its reaction with a thiophe...

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Scheme 2: Synthetic routes to S-CF₃ and Se-CF₃ dibenzochalcogenium salts.

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Scheme 3: Synthesis of (trifluoromethyl)dibenzotellurophenium salts.

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Scheme 4: Nitration of (trifluoromethyl)dibenzochalcogenium salts.

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Scheme 5: Synthesis of a sulphonium salt with a bridged oxygen.

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Scheme 6: Reactivity of (trifluoromethyl)dibenzochalcogenium salts.

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Scheme 7: Pd(II)-Catalyzed ortho-trifluoromethylation of heterocycle-substituted arenes by Umemoto’s reagents....

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Scheme 8: Mild electrophilic trifluoromethylation of β-ketoesters and silyl enol ethers.

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Scheme 9: Enantioselective electrophilic trifluoromethylation of β-ketoesters.

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Scheme 10: Preparation of water-soluble S-(trifluoromethyl)dibenzothiophenium salts.

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Scheme 11: Method for large-scale preparation of S-(trifluoromethyl)dibenzothiophenium salts.

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Scheme 12: Triflic acid catalyzed synthesis of 5-(trifluoromethyl)thiophenium salts.

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Scheme 13: Trifluoromethylation of β-ketoesters and dicyanoalkylidenes by S-(trifluoromethyl)benzothiophenium ...

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Scheme 14: Synthesis of chiral S-(trifluoromethyl)benzothiophenium salt 18 and attempt of enantioselective tri...

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Scheme 15: Synthesis of O-(trifluoromethyl)dibenzofuranium salts.

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Scheme 16: Photochemical O- and N-trifluoromethylation by 20b.

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Scheme 17: Thermal O-trifluoromethylation of phenol by diazonium salt 19a. Effect of the counteranion.

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Scheme 18: Thermal O- and N-trifluoromethylations.

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Scheme 19: Method of preparation of S-(trifluoromethyl)diphenylsulfonium triflates.

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Scheme 20: Reactivity of some S-(trifluoromethyl)diarylsulfonium triflates.

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Scheme 21: One-pot synthesis of S-(trifluoromethyl)diarylsulfonium triflates.

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Scheme 22: One-pot synthesis of Umemoto’s type reagents.

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Scheme 23: Preparation of sulfonium salts by transformation of CF₃⁻ into CF₃⁺.

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Scheme 24: Selected reactions with the new Yagupolskii reagents.

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Scheme 25: Synthesis of heteroaryl-substituted sulfonium salts.

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Scheme 26: First neutral S-CF₃ reagents.

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Scheme 27: Synthesis of Togni reagents. ^aYield for the two-step procedure.

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Scheme 28: Trifluoromethylation of C-nucleophiles with 37.

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Scheme 29: Selected examples of trifluoromethylation of S-nucleophiles with 37.

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Scheme 30: Selected examples of trifluoromethylation of P-nucleophiles with 35 and 37.

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Scheme 31: Trifluoromethylation of 2,4,6-trimethylphenol with 35.

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Scheme 32: Examples of O-trifluoromethylation of alcohols with 35 in the presence of 1 equiv of Zn(NTf₂)₂.

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Scheme 33: Formation of trifluoromethyl sulfonates from sulfonic acids and 35.

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Scheme 34: Organocatalytic α-trifluoromethylation of aldehydes with 37.

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Scheme 35: Synthesis of reagent 42 and mechanism of trifluoromethylation.

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Scheme 36: Trifluoromethylation of β-ketoesters and dicyanoalkylidenes with 42.

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Album

Review

Published 16 Jun 2010

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