Selectfluor, Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), F-TEDA-BF4
Recent Literature
A palladium-catalyzed synthesis of aryl fluorides from arylboronic acid
derivatives is operationally simple and amenable to multigram-scale synthesis.
Evaluation of the reaction mechanism suggests a single-electron-transfer pathway
that involves a Pd(III) intermediate.
A. R. Mazzotti, M. G. Campbell, P. Tang, J. M. Murphy, T. Ritter, J. Am. Chem. Soc., 2013,
135, 14012-14015.
A powerful free radical Markovnikov hydrofluorination of unactivated alkenes is
mediated by Fe(III)/NaBH4 using Selectfluor reagent as a source of
fluorine. In contrast to the traditional radical hydrofluorination of alkenes,
the Fe(III)/NaBH4-mediated reaction is conducted under exceptionally
mild reaction conditions, tolerates various functional groups, and even runs
open to the air and with water as a cosolvent.
T. J. Barker, D. L. Borger, J. Am. Chem. Soc., 2012,
134, 13588-13591.
Visible light activates diarylketone catalysts to abstract a benzylic hydrogen
atom selectively, which enables an operationally simple direct fluorination of
benzylic C-H groups in the presence of a fluorine radical donor. 9-Fluorenone
catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H
difluorination.
J.-B. Xia, C. Zhu, C. Chen, J. Am. Chem. Soc., 2013,
135, 17494-17500.
J.-B. Xia, C. Zhu, C. Chen, J. Am. Chem. Soc., 2013,
135, 17494-17500.
A continuous-flow protocol for the light-induced fluorination of benzylic
compounds in very good isolated yields in residence times below 30 min uses
Selectfluor as the fluorine source and xanthone as an inexpensive and
commercially available photoorganocatalyst. The flow photoreactor is based on
transparent fluorinated ethylene propylene tubing and a household compact
fluorescent lamp with black-light irradiation.
D. Cantillo, O. de Frutos, J. A. Rincón, C. Mateos, C. O. Kappe, J. Org. Chem., 2014,
79, 8486-8490.
A mild C-F functionalization of benzylic sp3 C-H bonds allows the
synthesis of monofluorinated benzylic substrates in the presence of commercially
available iron(II) acetylacetonate and Selectfluor in very good yields and
selectivity. A convenient route to β-fluorinated products of 3-aryl ketones
provides a synthetic equivalent to the difficult to accomplish conjugate
addition of fluoride to α,β-unsaturated ketones.
S. Bloom C. R. Pitts, R. Woltornist, A. Griswold, M. G. Holl, T. Lectka, Org. Lett., 2013,
15, 1722-1724.
In a direct fluorination of C(sp3)-H bonds, a catalytic N-oxyl
radical generated from N,N-dihydroxypyromellitimide abstracts the
hydrogen followed by trapping of the resulting carbon radical by Selectfluor.
This simple metal-free protocol enables the chemoselective introduction of a
fluorine atom into various aromatic and aliphatic compounds and serves as a
powerful tool for the efficient synthesis of fluorinated molecules.
Y. Amaoka, M. Nagamoto, M. Inoue, Org. Lett., 2013,
15, 2160-2163.
Activation of a hydroxyl group by a Ph2PCH2CH2PPh2/ICH2CH2I
system enables an efficient dehydroxylative fluorination of tertiary alcohols
with Selectfluor. The reaction occurs rapidly to give the desired products in
good yields.
W. Zhang, Y.-C. Gu, J.-H. Lin, J.-C. Xiao,
Org. Lett., 2020, 22, 6642-6646.
A catalytic amount of AgNO3 enables an efficient decarboxylative
fluorination of aliphatic carboxylic acids with Selectfluor in aqueous solution
to yield the corresponding alkyl fluorides in good yields under mild conditions.
This radical fluorination method is not only efficient and general but also
chemoselective and functional-group-compatible, thus making it highly practical
in the synthesis of fluorinated molecules.
F. Yin, Z. Wang, Z. Li, C. Li, J. Am. Chem. Soc., 2012,
134, 10401-10404.
Visible light-promoted photoredox catalysis enables a direct conversion of
aliphatic carboxylic acids to the corresponding alkyl fluorides. This
operationally simple, redox-neutral fluorination method allows the conversion of
a broad range of carboxylic acids.
S. Ventre, F. R. Petronijevic, D. W. C. MacMillan, J. Am. Chem. Soc., 2015,
137, 5654-5657.
Iodine catalyzes a simple and practical difluorination reaction of alkenes. The
reaction can be applied to many aliphatic and aromatic alkenes bearing
synthetically useful functional groups, such as ester, amide, hydroxy, and aryl
groups.
T. Kitamura, J. Oyamada, M. Higashi, Y. Kishikawa, J. Org. Chem., 2024, 89,
5896-5900.
A Ag-catalyzed decarboxylative fluorination reaction provides an
unprecedented route to either gem-difluoroalkanes or α-fluorocarboxylic
acids from malonic acid derivatives by the judicious selection of base and
solvent. This reaction features the use of readily available starting materials,
tunable chemoselectivity and good functional group compatibility.
Z. Wang, C.-Y. Guo, C. Yang, J.-P. Chen, J. Am. Chem. Soc.,
2019,
141, 5617-5622.
A divergent strategy for the fluorination of phenylacetic acid derivatives is
induced by a charge-transfer complex between Selectfluor and
4-(dimethylamino)pyridine. In the presence of water, decarboxylative
fluorination through a single-electron oxidation is dominant. Non-aqueous
conditions result in the clean formation of α-fluoro-α-arylcarboxylic acids.
A. Madani, L. Anghileri, M. Heydenreich, H. M. Möller, B. Pieber, Org. Lett.,
2022, 24, 5376-5380.
Sulfur mediates a synthesis of acyl fluorides from carboxylic acids using
Selectfluor. A broad range of acyl fluorides are accessible from carboxylic
acids while avoiding the formation of acid anhydrides. 19F NMR
spectra suggest that a S8-fluoro-sulfonium cation and a neutral S8-difluoride
are generated in situ as reactive species in this deoxyfluorination reaction.
E. M. Mahmoud, S. Mori, Y. Sumii, N. Shibata, Org. Lett., 2023, 25,
2810-2814.
A decarboxylative fluorination of tertiary β-keto carboxylic acids using an electrophilic fluorinating reagent proceeded in
the absence of a catalyst or base to yield the corresponding α-fluoroketones
very good yields.
M. Katada, K. Kitahara, S. Iwasa, K. Shibatomi, Synlett, 2018, 29,
2408-2411.
A Ag-catalyzed decarboxylative fluorination reaction provides an
unprecedented route to either gem-difluoroalkanes or α-fluorocarboxylic
acids from malonic acid derivatives by the judicious selection of base and
solvent. This reaction features the use of readily available starting materials,
tunable chemoselectivity and good functional group compatibility.
Z. Wang, C.-Y. Guo, C. Yang, J.-P. Chen, J. Am. Chem. Soc.,
2019,
141, 5617-5622.
Enantioselective α-fluorination of both cyclic and acyclic β-dicarbonyl
compounds with β,β-diaryl serines as primary amine organocatalysts was conducted
with only 1.1 equiv of Selectfluor by adding alkali carbonates, such as Na2CO3
or Li2CO3. The reaction afforded α-fluorinated
β-dicarbonyl compounds in good yield with excellent enantioselectivity.
K. Endo, D. Tomon, S. Arimitsu, J. Org. Chem., 2023, 88,
9037-9045.
A β,β-diaryl serine catalyzes an enantioselective fluorination of
α-substituted β-diketones to afford the corresponding fluorinated products in
very good yields with excellent enantioselectivity. The CO2H group of
the primary amine organocatalyst plays an important role in inducing the high
enantioselectivity. Products could be converted into diols, aldols, and allylic
fluorides without racemization.
S. Poorsadeghi, K. Endo, S. Arimitsu, Org. Lett., 2022, 24,
420-424.
By altering the amount of Selectfluor, a highly selective mono- and
difluorination of 1,3-dicarbonyl compounds provides various 2-fluoro- and
2,2-difluoro-1,3-dicarbonyl compounds in very good yields. This practical
and convenient fluorination can be performed in aqueous media without any
catalyst and base.
L. Tang, Z. Yang, J. Jiao, Y. Cui, G. Zou, Q. Zhou, Y. Zhou, W. Rao, X. Ma, J. Org. Chem., 2019,
84, 10449-10458.
By altering the amount of Selectfluor, a highly selective mono- and
difluorination of 1,3-dicarbonyl compounds provides various 2-fluoro- and
2,2-difluoro-1,3-dicarbonyl compounds in very good yields. This practical
and convenient fluorination can be performed in aqueous media without any
catalyst and base.
L. Tang, Z. Yang, J. Jiao, Y. Cui, G. Zou, Q. Zhou, Y. Zhou, W. Rao, X. Ma, J. Org. Chem., 2019,
84, 10449-10458.
A radical-based C-C bond scission of 1,1-disubstituted epoxides followed by
demethylenation provides ketones. The reaction is accomplished by Selecfluor and its radical dication working in tandem.
E. Holt, N. G. Garrison, R. Rowshanpour, J. J. Kim, N. Henriquez, W. Lam, N.
Kiame, J. Williams, S. Zhao, T. Dudding, T. Lectka, J. Org. Chem., 2023, 88,
7597-7600.
A convenient reaction of isoxazoles with an electrophilic fluorinating agent
(Selectfluor) provides tertiary fluorinated carbonyl compounds under mild
reaction conditions and with good functional group tolerance. Diverse
transformations of the resulting α-fluorocyanoketones furnish a broad range of fluorinated compounds.
M. Komatsuda, H. Ohki, H. Kondo Jr., A. Suto, J. Yamaguchi, Org. Lett.,
2022, 24, 3270-3274.
In a remote hydro-oxygenation of alkenes under palladium catalysis, both
terminal and internal alkenes are suitable to yield the corresponding linear
alcohols efficiently. A compatible SelectFluor/silane redox system plays an
essential role for the excellent chemo- and regioselectivities. The reaction
features a broad substrate scope and excellent functional group compatibility.
X. Li, X. Yang, P. Chen, G. Liu, J. Am. Chem. Soc.,
2022, 144, 22877-22883.
In a remote hydro-oxygenation of alkenes under palladium catalysis, both
terminal and internal alkenes are suitable to yield the corresponding linear
alcohols efficiently. A compatible SelectFluor/silane redox system plays an
essential role for the excellent chemo- and regioselectivities. The reaction
features a broad substrate scope and excellent functional group compatibility.
X. Li, X. Yang, P. Chen, G. Liu, J. Am. Chem. Soc.,
2022, 144, 22877-22883.
Photoredox catalysis enables a domino-fluorination-protodefluorination
decarboxylative cross-coupling of α-keto acids with styrene to provide
α,β-unsaturated ketones under mild conditions.
M. Zhang, J. Xi, R. Ruzi, N. Li, Z. Wu, W. Li, C. Zhu, J. Org. Chem.,
2017, 82, 9305-9311.
Gold catalysis enables a chemoselective α-methylenation of aromatic ketones
using Selectfluor as a methylenating agent to provide various 1,2-disubstituted
propenone derivatives in good yields. This reaction offers simple operation,
good functional group tolerance, and broad scope of substrates.
H. Zhu, X. Meng, Y. Zhang, G. Chen, Z. Cao, X. Sun, J. You, J. Org. Chem.,
2017, 82, 12059-12065.
Selectfluor-promoted cascade cyclizations and cross-coupling reactions provide
either 2,5-diacylthiophenes or β-acyl allylic methylsulfones from readily
available starting materials by simple solvent modification. The transformations
offer excellent chemoselectivity, and good functional group tolerance.
H. Lu, J. Chen, W. Zhou, L. Peng, S.-F. Yin, N. Kambe, R. Qiu, Org. Lett., 2023, 25,
389-394.
A catalytic, regioselective oxidative cyanation of conjugated and nonconjugated
alkenes using a homogeneous copper catalyst and Selectfluor as oxidant provides
branched alkenyl nitriles that are difficult to prepare.
D.-W. Gao, E. V. Vinogradova, S. K. Nimmagadda, J. M. Medina, Y. Xiao, R. M.
Suciu, B. F. Cravatt, K. M. Engle, J. Am. Chem. Soc.,
2018,
140, 8069-8073.
Selectfluor mediates an oxidative dehydrogenation of hydrazine derivatives
via N-fluorination and elimination processes to provide azo compounds.
This reaction offers simple operation, mild conditions, good functional group
tolerance, and high efficiency.
Y. Zhao, S. Li, J. Cui, H. Wang, X. King, Y. Wang, L. Tian, Synthesis, 2022, 54,
5245-5252.
A palladium pincer complex catalyzes an allylic C-H borylation of alkenes in
high yields. The transformation exhibits high regio- and stereoselectivity with
various linear alkenes. Preliminary mechanistic studies indicate that this C-H
borylation reaction proceeds via Pd(IV) pincer complex intermediates.
L. Mao, R. Bertermann, K. Emmert, K. J. Szabo, T. B. Marder, Org. Lett.,
2017, 19, 6586-6589.
A transition-metal-free chemo-, regio-, and stereoselective electrophilic
fluorodesilylation of α-silyl-substituted allylboronate esters with Selectfluor
provides a variety of (E)-boryl-substituted allyl fluorides in good
yields. Further modifications of the obtained (E)-boryl-substituted allyl
fluorides afford allyl or alkyl fluoride derivatives.
Y. Jung, S. H. Cho, Synlett, 2023,
34,
2165-2168.
A catalytic, vicinal difluorination of olefins displays broad functional group
tolerance, using inexpensive p-iodotoluene as the catalyst. Preliminary
efforts toward the development of an enantioselective variant are reported.
I. G. Molnár, R. Gilmour, J. Am. Chem. Soc., 2016,
138, 5004-5007.
The use of Selectfluor as an oxidant and tetrabutylammonium bromide/chloride
salts as a halogen source enables a metal-free and molecular halogen
reagent-free dihomohalogenation methodology. This effective strategy provides
various fluorine-free halogenated products easily in quantitative yields from
alkenes, alkynes, and natural products.
Z. Dağalan, R. Koçak, A. Daştan, B. Nişancı, Org. Lett., 2022, 24,
8261-8264.
A micellar system was developed and applied for direct regioselective
fluorination of various cyclic and acyclic ketones to α-fluoroketones in water
as reaction medium with Selectfluor (F-TEDA-BF4) as fluorinating
reagent. The inexpensive ionic amphiphile sodium dodecyl sulfate (SDS) was found
to be an excellent promoter.
G. Stavber, M. Zupan, S. Stavber, Synlett, 2009,
589-594.
An efficient and mild fluorination of vinyl azides enables the synthesis of
α-fluoroketones via a single-electron transfer (SET) and a subsequent fluorine
atom transfer.
S.-W. Wu, F. Liu, Org. Lett.,
2016, 18, 3642-3645.
Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2.
A subsequent reaction with Selectfluor present in the reaction media produces
α-fluoro ketones as single constitutional isomers in good yields.
N. Ahlsten, A. Bartoszewicz, S. Agrawal, B. Martín-Matute, Synthesis, 2011,
2600-2608.
A metal-free and green catalytic system enables an oxyfluorination of olefins
for the synthesis of α-fluoroketones which is an important building block for
organic synthesis. Moreover, this reaction system exhibits great functional
group tolerance.
Q. Yang, L.-L. Mao, B. Yang, S.-D. Yang, Org. Lett., 2014,
16, 3460-3463.
In an enantioselective fluorination of allylic alcohols under chiral anion
phase-transfer conditions, an in situ generation of a directing group proved
crucial for achieving effective enantiocontrol. In the presence of such a
directing group, a range of acyclic substrates underwent fluorination to afford
highly enantioenriched α-fluoro homoallylic alcohols.
W. Zi, Y.-M. Wang, F. D. Toste, J. Am. Chem. Soc., 2014,
136, 12864-12867.
A dianionic
phase-transfer catalyst enables an asymmetric fluorofunctionalization of γ,γ-disubstituted allylamine
derivatives. Depending on the substituents on the alkene moiety, the
reaction afforded chiral allylic fluorides and fluorinated dihydrooxazines in a
highly enantioselective manner.
T. Niwa, K. Nishibashi, H. Sato, K. Ujiie, K. Yamashita, H. Egami, Y.
Hamashima, J. Am. Chem. Soc.,
2021, 143, 16599-16609.
A combination of copper powder and Selectfluor generates a cationic copper
species that efficiently catalyze the formation of 1,2-diketones from alkynes
under mild conditions with water and dioxygen as inexpensive and environmentally
benign sources of oxygen.
W. Zhang, J. Zhang, Y. Liu, Z. Xu, Synlett, 2013, 24,
2709-2714.
A Selectfluor-mediated reaction of α,β-epoxy ketones provides 1,2-diketones in
good yields under transition-metal-free oxidative conditions via a ring-opening/benzoyl
rearrangement/C-C bond cleavage sequence.
H. Wang, S. Ren, J. Zhang, W. Zhang, Y. Liu, J. Org. Chem.,
2015,
80, 6856-6863.
Allenyl carbinol esters isomerize to an E,Z mixture of the corresponding
dienes in the presence of a gold catalyst. In a subsequent reaction with
Selectfluor, this mixture can be converted to monofluoroalkyl α,β-unsaturated
ketones with exclusive E selectivity in high yields.
Z. Jin, R. S. Hidinger, B. Xu, G. B. Hammond, J. Org. Chem., 2012,
77, 7725-7726.
Reactions of enamines with Selectfluor under mild conditions easily led to
the corresponding difluorinated carbonyl compounds in high yields.
W. Peng, J. M. Shreeve, J. Org. Chem., 2005,
70, 5760-5763.
Selective introduction of an iodine atom at the α-carbonyl position in various
aryl alkyl ketones was effectively achieved by reaction of target molecules with
elemental iodine in the presence of N-F reagents such as F-TEDA-BF4 (Selectfluor)
as iodination mediators and methanol as the solvent.
M. Jereb, S. Stavber, M. Zupan, Synthesis,
2003, 853-858.
Benzene derivatives bearing at least one bulky alkyl group (i-Pr or
t-Bu) were selectively and effectively iodinated using elemental iodine
activated by Selectfluor. Up to three iodine atoms were progressively introduced
at the most electron-rich and sterically less hindered position on the benzene
ring.
S. Stavber, P. Kralj, M. Zupan, Synthesis,
2002, 1513-1518.
A Ru(II) catalyzed ortho-hydroxylation of ethyl benzoates with ester as a
directing groups enables a facile synthesis of various multifunctionalized
arenes from easily accessible substrates. Crucial factors in this transformation
are both the TFA/TFAA cosolvent system and the oxidants. The reaction
demonstrates excellent reactivity, good functional group tolerance, and high
yields.
Y. Yang, Y. Lin, Y. Rao, Org. Lett., 2012,
14, 2874-2877.
Using commercially available Ph3PAuCl and readily prepared, benign
arylsilanes, a gold-catalyzed oxyarylation of alkenes proceeds smoothly in air.
The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold
but also provides a fluoride anion for silane activation, thereby avoiding the
need for addition of a stoichiometric base.
L. T. Ball, M. Green G. C. Lloyd-Jones, C. A. Russel, Org. Lett., 2010,
12, 4724-4727.
Oxidative bromination of different types of olefins
using Selectfluor/KBr afforded addition, monobromo-substituted, or
Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem.,
2004,
69, 8561-8563.
Oxidative bromination of different types of olefins
using Selectfluor/KBr afforded addition, monobromo-substituted, or
Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem.,
2004, 69, 8561-8563.
Selectfluor mediates practical and efficient oxidations of sulfides and
thiols to provide sulfoxides, sulfones, and thiosulfonates, respectively, at
ambient temperature. All these organosulfur compounds can be prepared with
nearly quantitative yields by applying eco-friendly H2O as O-source.
The formation of sulfoxides and thiosulfonates takes only a few minutes.
X. Guo, X. Sun, M. Jiang, Y. Zhao, Synthesis, 2022, 54,
1996-2004.
Selectfluor mediates practical and efficient oxidations of sulfides and
thiols to provide sulfoxides, sulfones, and thiosulfonates, respectively, at
ambient temperature. All these organosulfur compounds can be prepared with
nearly quantitative yields by applying eco-friendly H2O as O-source.
The formation of sulfoxides and thiosulfonates takes only a few minutes.
X. Guo, X. Sun, M. Jiang, Y. Zhao, Synthesis, 2022, 54,
1996-2004.
Selectfluor mediates practical and efficient oxidations of sulfides and
thiols to provide sulfoxides, sulfones, and thiosulfonates, respectively, at
ambient temperature. All these organosulfur compounds can be prepared with
nearly quantitative yields by applying eco-friendly H2O as O-source.
The formation of sulfoxides and thiosulfonates takes only a few minutes.
X. Guo, X. Sun, M. Jiang, Y. Zhao, Synthesis, 2022, 54,
1996-2004.
Electrophilic bromination or fluorination of homoallylic alcohol O-Bn ethers
triggers a diastereoselective hydride transfer to provide diastereomerically
enriched haloalkyl alcohols. A subsequent intramolecular nucleophilic
substitution affords tetrahydrofurans.
B. Wang, D. A. Gandamana, D. F. L. Rayo, F. Gagosz, S. Chiba,
Org. Lett., 2019, 21, 9179-9182.
A catalytic intramolecular cyclization of 2-alkynone O-methyl oximes and
subsequent fluorination proceeds smoothly at room temperature in the presence of
5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of
NaHCO3. This process features an efficient one-pot cascade route to
fluoroisoxazoles with high yields and high selectivity under mild reaction
conditions.
Y. Jeong, B.-I Kim, J. K. Lee, J.-S. Ryu, J. Org. Chem., 2014,
79, 6444-6455.
Iodine catalyzes a cascade reaction between enaminones, hydrazines, and DMSO in
the presence of Selectfluor to provide 1,4-disubstituted pyrazoles. DMSO plays a
dual role as the C1 source and the reaction medium. In addition, the
synthesis of 1,3,4-trisubstituted pyrazoles using aldehydes as alternative C1
building blocks has also been achieved.
H. Guo, L. Tian, Y. Liu, J.-P. Wan, Org. Lett., 2022, 24,
228-233.
Organoiodine(I/III) chemistry enables a metal-free, catalytic enantioselective intermolecular oxyamination
of aryl- and alkyl-substituted alkenes with N-(fluorosulfonyl)carbamate as a bifunctional
N,O-nucleophile with high enantioselectivity and
electronically controlled regioselectivity. The oxyaminated products can be
easily deprotected in one step to reveal free amino alcohols in high yields.
C. Wata, T. Hashimoto, J. Am. Chem. Soc.,
2021, 143, 1745-1751.
A chiral triazole-substituted iodoarene catalyzes an enantioselective
oxidative cyclization of N-allyl carboxamides to provide highly
enantioenriched oxazolines and oxazines. Quaternary stereocenters can be
constructed and, besides N-allyl amides, the corresponding thioamides and
imideamides are well tolerated as substrates.
A. H. Abazid, T.-N. Hollwedel, B. J. Nachtsheim, Org. Lett., 2021, 23,
5076-5080.
A cyclization of N-alkenylamides catalyzed by iodoarenes under oxidative
conditions enables the preparation of five-, six-, and seven-membered rings with
a range of substitutions. Preliminary data from the use of chiral iodoarenes as
precatalysts show that enantiocontrol is feasible.
A. Alhalib, S. Kamouka, W. J. Moran, Org. Lett.,
2015,
17, 1453-1456.
Treatment of several 3-substituted indoles, including derivatives of
tryptophan and serotonin, with Selectfluor in acetonitrile/water provides
3-substiuted 3-fluorooxindoles in very good yields.
Y. Takeuchi, T. Tarui, N. Shibata,
Org. Lett., 2000, 2, 639-642.
A facile method enables the construction of quaternary 3,3-disubstituted
2-oxindoles from 2-substituted indoles without a catalyst under mild conditions
via an iminium-intermediate-triggered 1,2-rearrangement.
X. Jiang, J. Yang, F. Zhang, P. Yu, P. Yi, Y. Sun, Y. Wang, Org. Lett.,
2016, 18, 3154-3157.
An efficient cyclization of enamino ketones in the presence of Selectfluor
provides various 3-fluorochromones (3-fluoro-4H-chromene-4-ones) in good
yields. This method offers simple operational procedures, a high purity of the
product, and excellent regioselectivity.
V. Kandula, P. K. Thota, P. Mallesham, K. Raghavulu, A. Chatterjee, S. Yennam,
M. Behera, Synlett, 2019,
30,
2295-2299.
Selectfluor promotes an oxidative coupling of quinoxalin-2(1H)-ones with
alcohols, amines, thiols at the C3-position under metal- and photocatalyst-free
conditions. The method offers a broad substrate scope including bioactive
molecules, mild reaction conditions, readily available coupling partners, high
yields, scalability and step-economy.
Sonam, V. N. Shinde, K. Rangan, A. Kumar, J. Org. Chem., 2023, 88,
2344-2357.
A one-pot Pd-catalyzed reaction of aryl iodides with DABSO and Selectfluor
provides aryl sulfonyl fluorides in good yields. Additionally, sulfonyl
fluorides can be converted to aryl sulfonamides and sulfonic esters using Cs2CO3
under mild conditions.
A. L. Tribby, I. Rodríguez, S. Shariffudin, N. D. Ball, J. Org. Chem.,
2017, 82, 2294-2299.
An organobismuth(III) complex bearing a bis-aryl sulfone ligand backbone
catalyzes a synthesis of sulfonyl fluorides from the corresponding (hetero)aryl
boronic acids in the presence of SO2 and Selectfluor. The catalytic protocol
affords excellent yields for a wide range of aryl and heteroaryl boronic acids,
displaying a wide functional group tolerance.
M. Magre, J. Cornella, J. Am. Chem. Soc.,
2021, 143, 21497-21502.
In a copper-free Sandmeyer-type fluorosulfonylation reaction with Na2S2O5
as the sulfur dioxide source and Selectfluor as fluorine source, aryldiazonium
salts are transformed into sulfonyl fluorides. In situ diazotization enables the
use of aromatic amines as substrates. The method offers broad functional group
tolerance, gram-scale synthesis and late-stage fluorosulfonylation.
T. Zhong, M.-K. Pang, Z.-D. Chen, B. Zhang, J. Weng, G. Lu,
Org. Lett., 2020, 22, 2941-2945.
Thioethers can be converted to thiocyanates via fluorium-initiated dealkylative
cyanation in the presence of selectfluor as the oxidant and trimethylsilyl
cyanide as the cyanation reagent. This method is user-friendly, operationally
simple, and step-economical.
Y. Chen, H. Qi, N. Chen, D. Ren, J. Xu, Z. Yang, J. Org. Chem., 2019, 84,
9044-9050.
An efficient electrophilic fluorination of secondary phosphine oxides with
Selectfluor provides direct access to phosphoric fluorides in good yield under
mild conditions. In addition, one-pot P-O bond construction is achieved in the
presence of water or alcohols to provide phosphinic acids or phosphinates.
Q. Chen, J. Zeng, X. Yan, Y. Huang, C. Wen, X. Liu, K. Zhang, J. Org. Chem.,
2016, 81, 10043-10048.
An efficient electrophilic fluorination of secondary phosphine oxides with
Selectfluor provides direct access to phosphoric fluorides in good yield under
mild conditions. In addition, one-pot P-O bond construction is achieved in the
presence of water or alcohols to provide phosphinic acids or phosphinates.
Q. Chen, J. Zeng, X. Yan, Y. Huang, C. Wen, X. Liu, K. Zhang, J. Org. Chem.,
2016, 81, 10043-10048.