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Molecules 2011, 16(8), 6432-6464; doi:10.3390/molecules16086432
Review

Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis

1,2
1 Laboratory for Organic and Bioorganic Chemistry, “Jožef Stefan” Institute, Jamova 39, 1000 Ljubljana, Slovenia 2 Centre of Excellence CIPKeBiP, Jamova 39, 1000 Ljubljana, Slovenia
Received: 14 June 2011 / Revised: 5 July 2011 / Accepted: 19 July 2011 / Published: 29 July 2011
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Abstract

SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications as a mediator in transformations of oxidizable functional groups or gold-catalyzed C-C and C-heteroatom oxidative coupling reactions, a catalyst in formation of various heterocyclic rings, a reagent or catalyst of various functionalizations of electron-rich organic compounds (iodination, bromination, chlorination, nitration, thiocyanation, sulfenylation, alkylation, alkoxylation), a catalyst of one-pot-multi-component coupling reactions, a catalyst of regioselective ring opening of epoxides, a deprotection reagent for various protecting groups, and a mediator for stereoselective rearrangement processes of bicyclic compounds are reviewed and discussed.
Keywords: SelectfluorTM F-TEDA-BF4; oxidative transformations; coupling reactions; halogenation SelectfluorTM F-TEDA-BF4; oxidative transformations; coupling reactions; halogenation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Stavber, S. Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis. Molecules 2011, 16, 6432-6464.

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