# Selectfluor
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Selectfluor
> Markdown URL: https://mediated.wiki/source/Selectfluor.md
> Source: https://en.wikipedia.org/wiki/Selectfluor
> Source revision: 1286036117
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443880836
| ImageFileL1=F-TEDA-BF4.svg
| ImageSizeL1=100px
| ImageFileR1=Selectfluor-from-xtal-3D-balls.png
| ImageSizeR1=100px
| IUPACName=1-(Chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate
| OtherNames=F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)
1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=140681-55-6
| EINECS = 414-380-4
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2007047
| PubChem= 2724933
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4P1ZA6R76D
| InChI = 1/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1
| InChIKey = TXRPHPUGYLSHCX-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = TXRPHPUGYLSHCX-UHFFFAOYSA-N
| SMILES = [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F
}}
|Section2={{Chembox Properties
| Formula=C7H14B2ClF9N2
| MolarMass=354.26 g/mol
| Appearance=colourless solid
| Density=
| MeltingPtC=190
| MeltingPt_notes= decomposes >80 °C, exact m.p. is uncertain[
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
'''Selectfluor''', a trademark of [Air Products and Chemicals](/source/Air_Products_and_Chemicals), is a [reagent](/source/reagent) in [chemistry](/source/chemistry) that is used as a [fluorine](/source/fluorine) donor. This compound is a derivative of the nucleophillic base [DABCO](/source/DABCO). It is a colourless salt that tolerates air and even water. It has been commercialized for use for [electrophilic fluorination](/source/electrophilic_fluorination).][{{cite book |doi=10.1002/047084289X.rc116.pub2|chapter=1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)|title=Encyclopedia of Reagents for Organic Synthesis|year=2007|last1=Banks|first1=R. Eric|last2=Murtagh|first2=Vincent|last3=An|first3=Ilhwan|last4=Maleczka|first4=Robert E.|isbn=978-0471936237}}]
==Preparation==
:550px|F-TEDA-BF4 synthesis
Selectfluor is synthesized by the ''N''-[alkylation](/source/alkylation) of [[DABCO|diazabicyclo[2.2.2]octane (DABCO)]] with [dichloromethane](/source/dichloromethane) in a [Menshutkin reaction](/source/Menshutkin_reaction), followed by [ion exchange](/source/ion_exchange) with [sodium tetrafluoroborate](/source/sodium_tetrafluoroborate) (replacing the chloride [counterion](/source/counterion) for the tetrafluoroborate). The resulting salt is treated with elemental fluorine and sodium tetrafluoroborate:[
The cation is often depicted with one skewed ethylene ((CH2)2) group. In fact, these pairs of CH2 groups are eclipsed so that the cation has idealized C3h [symmetry](/source/symmetry_group).
==Mechanism of fluorination==
Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an [SN2](/source/SN2_reaction) attack at fluorine. This distinction has not been decided.][{{cite journal|doi=10.1002/anie.200400648|title=Selectfluor: Mechanistic Insight and Applications|year=2005|last1=Nyffeler|first1=Paul T.|last2=Durón|first2=Sergio Gonzalez|last3=Burkart|first3=Michael D.|last4=Vincent|first4=Stéphane P.|last5=Wong|first5=Chi-Huey|journal=Angewandte Chemie International Edition|volume=44|issue=2|pages=192–212|pmid=15578736|doi-access=free}}] By using a charge-spin separated probe,[{{cite journal|last1=Tojo|first1=Sachiko|last2=Morishima|first2=Kazuhiro|last3=Ishida|first3=Akito|last4=Majima|first4=Tetsuro|last5=Takamuku|first5=Setsuo|title=Remarkable Enhancements of Isomerization and Oxidation of Radical Cations of Stilbene Derivatives Induced by Charge-Spin Separation|journal=The Journal of Organic Chemistry|volume=60|issue=15|year=1995|pages=4684–4685|issn=0022-3263|doi=10.1021/jo00120a004}}] it was possible to show that the electrophilic fluorination of stilbenes with Selectfluor proceeds through an SET/fluorine atom transfer mechanism.[{{cite journal|last1=Brandt|first1=Jochen R.|last2=Lee|first2=Eunsung|last3=Boursalian|first3=Gregory B.|last4=Ritter|first4=Tobias|title=Mechanism of electrophilic fluorination with Pd(iv): fluoride capture and subsequent oxidative fluoride transfer|journal= Chem. Sci.|volume=5|issue=1|year=2014|pages=169–179|issn=2041-6520|doi=10.1039/C3SC52367E|pmc=3870902|pmid=24376910}}]
In certain cases Selectfluor can [transfer fluorine to alkyl radicals](/source/radical_fluorination).[{{Cite journal|title = Recent advances in radical fluorination|journal = [Synthesis](/source/Synthesis_(journal))|year = 2015|pages = 2554–2569|volume = 47|issue = 17|doi = 10.1055/s-0034-1378824|first1 = J.-F.|last1 = Paquin|first2 = G.|last2 = Sammis|first3 = C.|last3 = Chatalova-Sazepin|first4 = R.|last4 = Hemelaere| s2cid=196807570 }}]
==Applications==
The conventional source of "electrophilic fluorine", i.e. the equivalent to the [superelectrophile](/source/superelectrophile) F+, is gaseous fluorine, which requires specialised equipment for manipulation. Selectfluor reagent is a salt, the use of which requires only routine procedures. Like F2, the salt delivers the equivalent of F+. It is mainly used in the synthesis of [organofluorine compound](/source/organofluorine_compound)s:[
350px|center
===Specialized applications===
Selectfluor reagent also serves as a strong oxidant, a property that is useful in other reactions in [organic chemistry](/source/organic_chemistry). [Oxidation](/source/Organic_oxidation) of [alcohol](/source/Alcohol_(chemistry))s and [phenols](/source/phenols). As applied to [electrophilic iodination](/source/electrophilic_iodination), Selectfluor reagent activates the I–I bond in I2 molecule.][{{Cite journal|last1=Stavber|first1=Stojan|last2=Kralj|first2=Petra|last3=Zupan|first3=Marko|date=2002-08-01|title=Progressive Direct Iodination of Sterically Hindered Alkyl Substituted Benzenes|journal=Synthesis|language=en|volume=2002|issue=11|pages=1513–1518|doi=10.1055/s-2002-33339|issn=0039-7881}}]
==Related reagents==
Similar to Selectfluor are ''N''-fluorosulfonimides:[{{cite book|doi=10.1002/0471264180.or069.02 |chapter=Electrophilic Fluorination with N–F Reagents |title=Organic Reactions |date=2008 |last1=Baudoux |first1=Jérôme |last2=Cahard |first2=Dominique |pages=1–326 |isbn=978-0-471-26418-7 }}]
center|444px
==References==
{{Reflist}}
== Patents ==
* {{patent|US|5459267|"1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts and their application as fluorinating agents"}}
* {{patent|US|55227493|"Fluorinated Sulfonamide Derivatives"}}
* {{patent|US|5086178|"Fluorinated Diazabicycloalkane Derivatives"}}
* {{patent|US|5473065|"Fluorinated Diazabicycloalkane Derivatives"}}
* {{patent|US|5442084|"Method of Selective Fluorination"}}
{{Tetrafluoroborates}}
Category:Reagents for organic chemistry
Category:Tetrafluoroborates
Category:Fluorinating agents
Category:Quaternary ammonium compounds
Category:Nitrogen heterocycles
Category:Chloromethyl compounds
Category:Substances discovered in the 1990s
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Adapted from the Wikipedia article [Selectfluor](https://en.wikipedia.org/wiki/Selectfluor) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Selectfluor?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.