130409-81-3Relevant academic research and scientific papers
Decarboxylative nucleophilic difluoromethylation of aldehydes and imines
Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang
, p. 4295 - 4297 (2018/07/13)
The high demand for the biologically active CF2H-molecules has stimulated significant efforts to develop efficient methods for the installation of CF2H functionality. We found that phenylsulfonyl difluoroacetate salt (PhSO2/sub
Decarboxylative difluoromethylation of aldehydes with PhSO2CF2COOK: A facile and efficient access to difluoromethylated carbinols
Zhu, Yu-Jun,Lei, Zhong-Liang,Huang, Da-Kang,Lian, Bo,Liu, Zhen-Jiang,Hu, Xiao-Jun,Liu, Jin-Tao
, p. 3184 - 3187 (2018/07/13)
A novel decarboxylative difluoromethylation reaction of PhSO2CF2COOK with aldehydes under metal- and ligand-free conditions has been developed. The reaction is very mild and tolerates a wide range of aldehydes (both enolizable and non-enolizable aldehydes), providing a facile and efficient method for the synthesis of structurally diverse difluoromethylated carbinols in moderate to excellent yields.
Aryl sulfuryl difluoroacetic salt compound, as well as preparation method and application thereof
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, (2017/08/10)
The invention discloses an aryl sulfuryl difluoroacetic salt compound, as well as a preparation method and application thereof. The aryl sulfuryl difluoroacetic salt compound reacts with aldehyde at room temperature to obtain an aryl sulfuryl substituted alpha-difluoromethyl alcohol compound. The aryl sulfuryl difluoroacetic salt compound has the beneficial effects of mild reaction condition, high product yield, few side effect and high universality when the aryl sulfuryl difluoroacetic salt compound is adopted to prepare the aryl sulfuryl substituted alpha-difluoromethyl alcohol compound.
Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene
Motherwell, William B.,Greaney, Michael F.,Tocher, Derek A.
, p. 2809 - 2815 (2007/10/03)
Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.
α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms
Toyota, Akemi,Ono, Yoshinori,Chiba, Jun,Sugihara, Takumichi,Kaneko, Chikara
, p. 703 - 708 (2007/10/03)
Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.
Power and structure-variable fluorinating agents. The N-fluoropyridinium salt system
Umemoto, Teruo,Fukami, Shinji,Tomizawa, Ginjiro,Harasawa, Kikuko,Kawada, Kosuke,Tomita, Kyoichi
, p. 8563 - 8575 (2007/10/02)
The usefulness of the N-fluoropyridinium salt system as a source of fluorinating agents was examined by using substituted or unsubstituted N-fluoropyridinium triflates 1-11, N-fluoropyridinium salts possessing other counteranions 1a-d and 3a, and the counteranion-bound salts, N-fluoropyridinium-2-sulfonates 12 and 13. Electrophilic fluorinating power was found to vary remarkably according to the electronic nature of the ring substituents. This power increased as the electron density of positive nitrogen sites decreased, and this was correlated to the pKa values of the corresponding pyridines. By virtue of this variation, it was possible to fluorinate a wide range of nucleophilic substrates differing in reactivity. It is thus possible to fluorinate aromatics, carbanions, active methylene compounds, enol alkyl or silyl ethers, vinyl acetates, ketene silyl acetals, and olefins through the proper use of salts pentachloro 6 through 2,4,6-trimethyl 2, their power decreasing in this order. All the reactions could be explained on the basis of a one-electron-transfer mechanism. N-Fluoropyridinium salts showed high chemoselectivity in fluorination, the extent depending on the reactive moiety. In consideration of these Findings, selective 9α-fluorination of steroids was carried out by reacting 1 with tris(trimethylsilyl ether) 73 of a triketo steroid. Regio- or stereoselectivity in fluorination was determined by a N-fluoropyridinium salt structure. Steric bulkiness of the N-F surroundings hindered the ortho fluorination of phenols and aniline derivatives, while the capacity for hydrogen bonding on the part of the counteranions prompted this process, and the counteranion-bound salts 12 and 13 underwent this fluorination exclusively or almost so. Both bulky N-fluoropyridinium triflates 2 and 7 preferentially attacked the 6-position of the conjugated vinyl ester of a steroid from the unhindered β-direction to give a thermally unstable 6β-fluoro isomer. On the basis of these results, N-fluoropyridinium salts may be concluded to constitute a system that can serve as a source of the most ideal fluorinating agents for conducting desired selective fluorination through fluorinating capacity or structural alteration.
