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. 2017 Sep 15;82(18):9263-9269.
doi: 10.1021/acs.joc.7b01850. Epub 2017 Sep 5.

Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry

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Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry

Bibek Dhakal et al. J Org Chem. .
Free PMC article

Abstract

Although the triflate ion is not generally perceived as a nucleophile, many examples of its behavior as such exist in the literature. This Synopsis presents an overview of such reactions, in which triflate may be either a stoichiometric or catalytic nucleophile, leading to the suggestion that nucleophilic catalysis by triflate may be more common than generally accepted, albeit hidden by the typical reactivity of organic triflates which complicates their observation as intermediates.

Figures

Scheme 1
Scheme 1
Triflate Synthesis by Metathesis
Scheme 2
Scheme 2
Preparation of 1,4-Ditrifloxybutane
Scheme 3
Scheme 3
Preparation of Ethyl Triflate from Diethyl Ether
Scheme 4
Scheme 4
Ring Opening of a Spiro Compound on Treatment with Triflic Anhydride
Scheme 5
Scheme 5
Rearrangement of β-Pericyclocamphanone with a Triflic Acid and Anhydride Mixture
Scheme 6
Scheme 6
Reaction of a Non-enolizable Ketone with Triflic Anhydride
Scheme 7
Scheme 7
Triflate Formation by Electrophilic Addition to Alkenes
Scheme 8
Scheme 8
Competitive Cation Trapping by Triflate in Acetic Acid
Scheme 9
Scheme 9
Solvent Dependence in the Addition of Triflic Acid to 1-Pentene
Scheme 10
Scheme 10
Reaction of Alkenes with Zefirov’s Reagent
Scheme 11
Scheme 11
Reaction of a Silyl Enolether with Iodosobenzene and TMSOTf
Scheme 12
Scheme 12
Reaction of Phenylfluoroiodonium Triflate with 1-Hexyne
Scheme 13
Scheme 13
Generation of Fluoroalkyl Vinyl Triflates from Alkynes
Scheme 14
Scheme 14
Synthesis of Triflates from Sulfuranes
Scheme 15
Scheme 15
Addition of Triflate to Aryl Nitrenium Ions
Scheme 16
Scheme 16
Addition of Triflic Acid to an Aryl Alkynyl Ketone
Scheme 17
Scheme 17
Triflate as Nucleophile in Deamination
Scheme 18
Scheme 18
Generation of a Mannosyl Triflate from the Sulfoxide
Scheme 19
Scheme 19
Counterion-Dependent Pathways for Silyl Transfer in the Mukaiyama Aldol Reaction
Scheme 20
Scheme 20
Triflate-dependent Enantioselectivity in the Trialkylsilyl Triflate-catalyzed [4+3] Cycloadditions of Epoxy Enolsilanes with Dienes (endo-adducts only illustrated)
Scheme 21
Scheme 21
β-Selective Mannosylation with only Catalytic Triflic Acid
Scheme 22
Scheme 22
Diverging Reaction Pathways on the Activation of β-Mannopyranosyl Trichloroacetimidates with Triflate and Triflimde-Based Promoters
Scheme 23
Scheme 23
Counterion-dependent Mechanisms in Gold-Catalyzed β-Mannosylations (Illustrated for the β-donor only)

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