1481-36-3Relevant academic research and scientific papers
Stabilization of Photocatalytically Active Uranyl Species in a Uranyl - Organic Framework for Heterogeneous Alkane Fluorination Driven by Visible Light
Zhang, Xuan,Li, Peng,Krzyaniak, Matthew,Knapp, Julia,Wasielewski, Michael R.,Farha, Omar K.
, (2020)
When photoactivated, the uranyl ion is a powerful oxidant capable of abstracting hydrogen atoms from nonactivated C-H bonds. However, the highly reactive singly reduced [UVO2]+intermediate is unstable with respect to disproportionation to the uranyl dication and insoluble tetravalent uranium phases, which limits the usage of uranyl ions as robust photocatalysts. Herein, we demonstrate that photoactivated uranyl ions can be stabilized by immobilizing and separating them spatially in a uranyl-organic framework heterogeneous catalyst, NU-1301. The visible-light-photoactivated uranyl ions in NU-1301 exhibited longer-lived U(V) and radicals than those in homogeneous counterparts, as evidenced by X-ray photoelectron spectroscopy and time-dependent electron paramagnetic resonance, leading to higher turnovers and enhanced stability for the fluorination of nonactivated alkanes.
MELAMINE-HYDROGEN FLUORIDE SOLUTION. A HIGHLY EFFECTIVE AND CONVENIENT HYDROFLUORINATION REAGENT OF ALKENES
Yoneda, Norihiko,Abe, Takafumi,Fukuhara, Tsuyoshi,Suzuki, Akira
, p. 1135 - 1136 (1983)
A solution of 14percent (w/w) melamine in 86percent (w/w) hydrogen fluoride has been found to be stable, and more convenient and effective hydrofluorinating reagent for alkenes than those of other organic amine-hydrogen fluoride reagents.
The Uranyl Cation as a Visible-Light Photocatalyst for C(sp3)?H Fluorination
West, Julian G.,Bedell, T. Aaron,Sorensen, Erik J.
, p. 8923 - 8927 (2016)
The fluorination of unactivated C(sp3)?H bonds remains a desirable and challenging transformation for pharmaceutical, agricultural, and materials scientists. Previous methods for this transformation have used bench-stable fluorine atom sources; however, many still rely on the use of UV-active photocatalysts for the requisite high-energy hydrogen atom abstraction event. Uranyl nitrate hexahydrate is described as a convenient, hydrogen atom abstraction catalyst that can mediate fluorinations of certain alkanes upon activation with visible light.
Efficient protocol for the SO2F2-mediated deoxyfluorination of aliphatic alcohols
Lee, Cayo,Lai, Joey,Epifanov, Maxim,Wang, Cindy Xinyun,Sammis, Glenn M.
supporting information, (2021/09/28)
Alkyl fluorides are prevalent in both the pharmaceutical and agrochemical industries. As such, there has been significant interest over the past 40 years in the development of new synthetic methods to access these important fluorinated motifs. Herein we report the sulfuryl fluoride-mediated deoxyfluorination of alcohols using room temperature reaction conditions in only an hour. A wide range of primary aliphatic alcohols were efficiently converted to the corresponding fluoride in 46-70% isolated yields. Secondary alcohols were also effectively deoxyfluorinated in 50–92% yields. Chiral secondary alcohols were cleanly converted to the corresponding alkyl fluoride with only a minor deterioration of the enantioenrichment. A steroid derivative also underwent deoxyfluorination in 50% yield and 5.9:1 dr, with the major product resulting from net inversion of the stereocenter.
Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor
González-Esguevillas, María,Miró, Javier,Jeffrey, Jenna L.,MacMillan, David W.C.
supporting information, p. 4222 - 4227 (2019/06/13)
Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.
Manufacturing method for amino-substituted phosphazene compound, manufacturing method for electrolyte solution for nonaqueous secondary battery, and manufacturing method for nonaqueous secondary battery
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Page/Page column 25; 26, (2018/08/07)
Provided are a manufacturing method for an amino-substituted phosphazene compound including reacting a fluorinated phosphazene compound and an amine compound in presence of a compound having a fluorine trapping function; and synthesizing a compound obtained by substituting the amine compound for the fluorinated phosphazene compound, a manufacturing method for an electrolyte solution for a nonaqueous secondary battery using this, and a manufacturing method for a nonaqueous secondary battery.
Process for producing fluoro-compounds
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Page/Page column 3, (2009/02/11)
The present invention provides a process for producing highly pure fluoro-compounds by making use of less costly and readily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products. Specifically
PROCESS FOR PRODUCTION OF FLUOROCOMPOUNDS
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Page/Page column 8-9, (2008/06/13)
A process for production of fluorocompounds by which high-purity fulorocompounds can be produced with inexpensive and easily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine while inhibiting the formation of chloride by-products, namely, a process
Method for producing organic compounds by substituting halogen atoms
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Page 16, (2008/06/13)
The invention pertains to a method in which a halogen atom of an organic compound is replaced with a group derived from a nucleophilic agent, at high yield and high efficiency, by the following method which includes a step of reacting the nucleophilic agent with an organic material having a halogen atom bonded to a carbon atom having four σ bonds, more specifically: a method for producing an organic compound having Q, the method including a step of reacting a compound represented by general formula (2) with an organic starting material having at least one halogen atom bonded to a carbon atom having four σ bonds so as to replace the halogen atom in the organic starting material with Q:MQa (wherein M represents an alkali metal atom, an alkali earth metal atom, or a rare earth metal atom; Q represents a moiety of an inorganic acid or an active hydrogen compound derived by eliminating a proton, wherein Q is a halogen atom different from the halogen atom in the organic starting material having the halogen atom bonded to the carbon atom having the four σ bonds; and a represents an integer of 1 to 3) in the presence of a compound represented by general formula (1) (wherein Z- represents an anion derived by eliminating a proton from an inorganic acid or an active hydrogen compound; R2 is the same or different; R2 each independently represent a C1-C10 hydrocarbon group or two R2 on the same nitrogen atom may be bonded with each other to form a ring with the nitrogen atom).
1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent
Petrov,Swearingen,Hong,Chris Petersen
, p. 25 - 31 (2007/10/03)
The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.
