70353-93-4Relevant academic research and scientific papers
Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group
Bode, Bela E.,Chabbra, Sonia,Champion, Sue,Dawson, Daniel M.,Sood, D. Eilidh,Sutherland, Andrew,Watson, Allan J. B.
supporting information, p. 8460 - 8463 (2020/04/10)
Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.
Application of bidentate phosphite ester ligand in C-F bond construction reaction
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Paragraph 0018-0024, (2019/01/08)
The invention discloses an application of a bidentate phosphite ester ligand in C-F bond construction reaction. The bidentate phosphite ester ligand with different connecting structures can be appliedto the C-F bond construction reaction in the presence of an iron catalyst; under the co-catalytic effect of the ligand and iron salt, fluoridation of allyl alcohols occurs in an organic solvent; thebidentate phosphite ester ligand has a formula as shown in the specification; in the formula, Linker is one of 1,2-propylene glycol and glycol; a Linker is formed by removing H from hydroxy of corresponding diol and then linking with P; the bidentate phosphite ester ligand is used for catalyzing allyl fluoridation, the catalytic system is high in reaction activity and the substrate is wide in universality; in the catalytic system for constructing C-F bond and compounding different fluorine-containing organic compounds, the dosage of the reaction catalyst is low.
Tetramethylfluoroformamidinium hexafluorophosphate (TFFH) as a mild deoxofluorination reagent
Bellavance, Gabriel,Dubé, Pascal,Nguyen, Bao
experimental part, p. 569 - 572 (2012/04/17)
The solid, air-stable peptide coupling reagent TFFH (tetramethylfluoroformamidinium hexafluorophosphate) was found to activate a variety of alcohols towards deoxofluorination. These conditions are compatible with carbonyl functional groups thus offering interesting possibilities for the application to sensitive molecules. Georg Thieme Verlag Stuttgart · New York.
Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride
Ramsden, Christopher A.,Shaw, Maxine M.
experimental part, p. 3321 - 3324 (2009/08/09)
The reactions of structurally diverse carboxylic acids with XeF2 in both CH2Cl2/Pyrex and CH2Cl2/PTFE have been studied. Pyrex appears to be a very effective heterogeneous catalyst for an electrophilic mode of reaction of polarised XeF2, leading to rearrangement, cyclisation and cationic products. In CH2Cl2/PTFE, fluorodecarboxylation is the main mode of reaction, in accordance with previous studies, and may occur via a SET reaction of unpolarised XeF2.
Practical and general method for direct synthesis of alkyl fluorides from alcohols under mild conditions
Bandgar, Babasaheb P.,Kamble, Vinod T.,Biradar, Ankush V.
, p. 1579 - 1582 (2007/10/03)
A variety of alcohols were treated with Ph 3P and KF in CCl 4-DMF at room temperature to afford the corresponding fluorides in very good yields. Springer-Verlag 2005.
Efficient and selective halogenation of allylic and benzylic alcohols under mild conditions
Bandgar, Babasaheb P.,Bettigeri, Sampada V.
, p. 1251 - 1255 (2007/10/03)
A simple, mild, and high yielding procedure for the halogenation of allylic and benzylic alcohols using a combination of SOCl2, benzotriazole, and potassium halides in DMF is described. The effectiveness of the protocol is manifested in its selectivity towards allylic and benzylic alcohols whereas other simple alcohols such as primary, secondary, and tertiary are found to be unreactive. Springer-Verlag 2004.
Novel Synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic Alcohols: A Copper(I) Iodide-initiated Trifluoromethyl-Dehydroxylation Process
Duan, Jian-Xing,Chen, Quing-Yun
, p. 725 - 730 (2007/10/02)
Benzyl, prop-2-enyl and allyl chlorodifluoroacetates 3a, bromodifluoroacetates 3b or fluorosulfonyldifluoroacetates 3c, when decomposed in the presence of 1 equivalent of copper(I) iodide at an appropriate temperature in dimethylformamide, gave the corresponding trifluoromethyl derivatives in good to excellent yields.The products can also be obtained directly by ester exchange of XCF2CO2Et (X = FSO2, Cl, Br) 6 and the corresponding alcohols in the presence of KF and CuI.A trifluoromethylation-dehydroxylation mechanism, initiated by CuI, is proposed.
A Facile Method for the Fluorine Substitution of Phenylthio Group via Sulfonium Salts Using Cesium Fluoride
Ichikawa, Junji,Sugimoto, Ken-ichi,Sonoda, Takaaki,Kobayashi, Hiroshi
, p. 1985 - 1988 (2007/10/02)
Monofluorinated compounds are easily prepared in good yields by treating phenyl sulfides with methyl fluorosulfonate and cesium fluoride in refluxing dichloromethane, successively.This reaction proceeds under so mild conditions as not to affect the coexisting bromine substituent.
