- Visible-Light-Induced Selective Photolysis of Phosphonium Iodide Salts for Monofluoromethylations
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The sigma (σ)-hole effect has emerged as a promising tool to construct novel architectures endowed with new properties. A simple yet effective strategy for the generation of monofluoromethyl radicals is a continuing challenge within the synthetic communit
- Chen, Xiang-Yu,Liu, Qiang,Lu, Yu,Sheng, He,Su, Xiao-Di,Wang, Zhi-Xiang,Zhang, Chao-Shen
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supporting information
p. 25477 - 25484
(2021/10/25)
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- Merging hypervalent iodine and sulfoximine chemistry: A new electrophilic trifluoromethylation reagent
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Electrophilic trifluoromethylation is at the forefront of methodologies available for the installation of the CF3 moiety to organic molecules; research in this field is largely spurred by the availability of stable and accessible trifluoromethy
- Kalim, Jorna,Duhail, Thibaut,Le, Thanh-Nghi,Vanthuyne, Nicolas,Anselmi, Elsa,Togni, Antonio,Magnier, Emmanuel
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p. 10516 - 10523
(2019/12/02)
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- Siladifluoromethylation and Deoxo-trifluoromethylation of PV-H Compounds with TMSCF3: Route to PV-CF2- Transfer Reagents and P-CF3 Compounds
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A method for siladifluoromethylation of dialkyl phosphonates and secondary phosphine oxides with TMSCF3 to produce nucleophilic PV-CF2- transfer reagents is disclosed, with multigram scale reactions included. Condition-dependent divergent reactivity under the established conditions is demonstrated by the formation of trifluoromethylphosphines. Both one-pot transformations are operationally simple and employ inexpensive materials. Mechanistic investigations suggest the divergent reactivity originates from a common intermediate, with Li+ concentration directing the chemoselectivity.
- Krishnamurti, Vinayak,Barrett, Colby,Prakash, G. K. Surya
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supporting information
p. 1526 - 1529
(2019/03/07)
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- Borazine-CF3? Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation
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A fluoroform-derived borazine CF3? transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C?H and C?X trifluoromethylation reactions. Mechanistic analysis supports a dissociative mechanism for CF3? transfer, and cation modification afforded a reagent with enhanced stability.
- Geri, Jacob B.,Wade Wolfe, Michael M.,Szymczak, Nathaniel K.
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supporting information
p. 1381 - 1385
(2018/01/15)
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- Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations
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A new class of electrophilic phosphonium cations (EPCs) containing a -CF3 group attached to the phosphorus(v) center is readily accessible in high yields, via a scalable process. These species are stable to air, water, alcohol and strong Br?nsted acid, even at raised temperatures. Thus, P-CF3 EPCs are more robust than previously reported EPCs containing P-X moieties (X = F, Cl, OR), and despite their reduced Lewis acidity they function as Lewis acid catalysts without requiring anhydrous reaction conditions.
- Fasano,LaFortune,Bayne,Ingleson,Stephan
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supporting information
p. 662 - 665
(2018/02/06)
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- A novel method for preparing S-(perfluoroalkyl)-dibenzothiophenium trifluoromethanesulfonate
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A method for preparing S-(perfluoroalkyl)-dibenzothiophenium trifluoromethanesulfonate shown as a general formula (I) by a one-pot process with significant effects is disclosed by the invention. The method includes reacting a biphenyl compound, perfluoroalkyl sulfonate, trifluoroacetic anhydride and trifluoromethanesulfonic acid. The biphenyl compound can be recovered and utilized so that the method is an environmentally friendly preparing method.
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Paragraph 0100; 0104
(2018/04/01)
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- COMPLEXES FOR NUCLEOPHILIC, RADICAL, AND ELECTROPHILIC POLYFLUOROALKYLATION
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Disclosed herein are borazine complexes and use of the same in perfluoroalkylation reactions.
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Paragraph 00135
(2018/04/11)
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- Powerful, Thermally Stable, One-Pot-Preparable, and Recyclable Electrophilic Trifluoromethylating Agents: 2,8-Difluoro- and 2,3,7,8-Tetrafluoro-S-(trifluoromethyl)dibenzothiophenium Salts
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Although many electrophilic trifluoromethylating agents have been reported to date, practically useful reagents have yet to be developed. S-(Trifluoromethyl)dibenzothiophenium salts, known as Umemoto's reagents, have two significant drawbacks that have ha
- Umemoto, Teruo,Zhang, Bin,Zhu, Tianhao,Zhou, Xiaocong,Zhang, Peng,Hu, Song,Li, Yuanqiang
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p. 7708 - 7719
(2017/08/14)
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- HALOGENATED S-(PERFLUOROALKYL) DIBENZOTHIOPHENIUM SALT AND ITS PRODUCTION METHODS
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Halogenated S-(perfluoroalkyl) dibenzothiophenium salt represented by the following general formula (I). This compound is a new, reactive, and industrially useful reagent for perfluoroalkylating organic compounds. The reagent can be prepared by a one-pot process or a two-step reaction process from a halogenated biphenyl and easily isolated by a filtration method. In addition, the halogenated biphenyl can be recovered by desulfurization from a halogenated dibenzothiophene obtained as a side-product by the usage of the reagent.
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Page/Page column 30-31
(2016/07/27)
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- Fluoroalkenyl, fluoroalkynyl and fluoroalkyl phosphines
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A review of the methods available for the preparation of monodentate P(III) compounds containing fluoroalkenyl, fluoroalkynyl and fluoroalkyl groups is given. The synthesis, properties and coordination chemistry of some fluoroalkenyl- and fluoroalkynyl-co
- Banger, Kulbinder K.,Brisdon, Alan K.,Herbert, Christopher J.,Ghaba, Hana Ali,Tidmarsh, Ian S.
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experimental part
p. 1117 - 1129
(2010/07/20)
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- A generic route to fluoroalkyl-containing phosphanes
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The reaction of trimethylsilyl-containing phosphanes with perfluoroiodoalkanes provides a general and convenient route to perfluoroalkyl-containing phosphanes. The Royal Society of Chemistry 2009.
- Brisdon, Alan K.,Herbert, Christopher J.
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supporting information; experimental part
p. 6658 - 6660
(2010/04/01)
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- Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(III)-CF3 reagents
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A direct, mild and efficient trifluoromethylation of primary and secondary phosphines is achieved with easily accessible, cheap hypervalent iodine compounds acting as electrophilic CF3-transfer reagents. The Royal Society of Chemistry.
- Eisenberger, Patrick,Kieltsch, Iris,Armanino, Nicolas,Togni, Antonio
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p. 1575 - 1577
(2008/12/21)
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- Recent advances in electrophilic CF3-transfer using hypervalent iodine(III) reagents
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The development of new methodologies for an efficient introduction of CF3 groups into complex molecules constitutes one of the most challenging tasks of modern organic chemistry. Recently, we reported the access to a new class of electrophilic CF3-transfer reagents based on hypervalent iodine. The versatile application of these reagents to C-centred nucleophiles, such as β-keto esters, silyl enol ethers and α-nitro esters, as well as to thiols and primary and secondary phosphines is described. Experiments with phenols afforded corresponding trifluomethylethers in very low yields. Schweizerische Chemische Gesellschaft.
- Kieltsch, Iris,Eisenberger, Patrick,Stanek, Kyrill,Togni, Antonio
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scheme or table
p. 260 - 263
(2009/04/07)
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- The synthesis of tris(perfluoroalkyl)phosphines
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Tris(perfluoroalkyl)phosphines, of interest as turtable alternatives to the carbon monoxide ligand, can be synthesised by the nucleophile mediated reaction of perfluoroalkyltrimethylsilanes with triphenylphosphite; the method can be extended to diphosphines. The Royal Society of Chemistry 2005.
- Murphy-Jolly, Makeba B.,Lewis, Lesley C.,Caffyn, Andrew J. M.
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p. 4479 - 4480
(2007/10/03)
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- Cyanide initiated perfluoroorganylations with perfluoroorgano silicon compounds
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Cyanophenylphosphanes, Ph2PCN or PhP(CN)2, do not react with Me3SiCF3 or Me3SiC6F5 in the absence of cyanide ions. Catalytic amounts of ionic cyanides such as [NEt4]CN
- Panne, Patricia,Naumann, Dieter,Hoge, Berthold
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p. 283 - 286
(2007/10/03)
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- Haloalkylation process
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A process for the haloalkylation of certain tin, phosphorus and germanium halides is disclosed. The process is carried out typically in a halocarbon solvent at temperatures of less than 0° C. using as the haloalkylating reagent an admixture of a haloalkyl halide and tris(lower alkylamino)phosphine.
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