Novel synthesis of desymmetrized resorcinol derivatives: Aryl fluoride displacement on deactivated substrates
A short, high-yielding synthesis of differentially substituted resorcinol derivatives has been developed that utilizes 1,3-difluorobenzene as the starting material and employs sequential nucleophilic aromatic substitution (S NAr) reactions to generate desymmetrized products. The scope and limitations of the second SNAr reaction on the deactivated 1-alkoxy-3-fluorobenzene intermediates have been investigated. This methodology has also been employed in the synthesis of desymmetrized catechol derivatives from 1,2-difluorobenzene.
Kim, Aujin,Powers, Jeremiah D.,Toczko, Jennifer F.
List fluoro Radicamine compounds and their use and preparation method
The invention discloses a mono-fluorinated Radicamine compound which has a structure as shown in a formula (1), and further provides a preparation method for the mono-fluorinated Radicamine compound with the structure as shown in the formula (1) and an application of the mono-fluorinated Radicamine compound or the mono-fluorinated Radicamine compound prepared with the method to preparation of drugs for preventing and/or treating diabetes, drugs for preventing and/or treating Gaucher's diseases, drugs for preventing and/or treating tumors or antiviral drugs. The mono-fluorinated Radicamine compound provided by the invention is good in glycosidase inhibition activity.
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Paragraph 0076-0078
(2017/12/02)
Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition
Fluorinated derivatives of radicamine A and radicamine B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies showed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom. C-7 or C-11 fluorination of the aromatic ring decreased α-glucosidase inhibition of the derivatives, whereas C-8 or C-10 fluorination preserved glycosidase inhibitory activities. Fluorinated derivatives of radicamine A and B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies revealed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom.
Li, Yi-Xian,Iwaki, Ren,Kato, Atsushi,Jia, Yue-Mei,Fleet, George W. J.,Zhao, Xuan,Xiao, Min,Yu, Chu-Yi
p. 1429 - 1438
(2016/03/16)
Synthesis of aryl fluorides from potassium aryltrifluoroborates and selectfluor mediated by iron(III) chloride
The synthesis of fluorinated arenes by the iron-mediated fluorination of potassium aryltrifluoroborates with Selectfluor and potassium fluoride is described. The fluorination reaction uses commercially available reagents and without requiring the addition
Electrophilic fluorination of cationic Pt-aryl complexes
The electrophilic fluorination of several (triphos)Pt-aryl+ establishes the first example of aryl-F coupling from a Pt center.
Zhao, Shu-Bin,Wang, Rui-Yao,Nguyen, Ha,Becker, Jennifer J.,Gagne, Michel R.
supporting information; experimental part
p. 443 - 445
(2012/01/14)
Metal-free electrophilic fluorination of alkyl trifluoroborates and boronic acids
Secondary alkyl trifluoroborates undergo facile electrophilic fluorination under mild conditions to afford the corresponding benzylic fluorinated adducts in excellent yield.
Cazorla, Clément,Métay, Estelle,Andrioletti, Bruno,Lemaire, Marc
experimental part
p. 3936 - 3938
(2009/09/30)
Practical synthesis of aromatic ethers by SNAr of fluorobenzenes with alkoxides
Aromatic fluorines have been substituted by alkoxides in a variety of activated and unactivated aromatic systems.