369-41-5Relevant academic research and scientific papers
Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene
Djukanovic, Dimitrije,Filipponi, Paolo,Heinz, Benjamin,Knochel, Paul,Mandrelli, Francesca,Martin, Benjamin,Mostarda, Serena
supporting information, p. 13977 - 13981 (2021/09/13)
The continuous flow reaction of various aryl or heteroaryl bromides in toluene in the presence of THF (1.0 equiv) with sec-BuLi (1.1 equiv) provided at 25 °C within 40 sec the corresponding aryllithiums which were acylated with various functionalized N,N-
Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols
Fan, Jiajie,Lin, Xianfu,Peng, Yongzhen,Wang, Anlin,Wu, Qi,Xu, Jian,Xu, Weihua,Yu, Huilei
supporting information, (2020/07/24)
A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92percent) and stereoselectivities (up to 99percent). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.
α-Fluorotricarbonyl Derivatives as Versatile Fluorinated Building Blocks: Synthesis of Fluoroacetophenone, Fluoroketo Ester and Fluoropyran-4-one Derivatives
Harsanyi, Antal,Lückener, Anne,Pasztor, Hedvig,Yilmaz, Zahide,Tam, Lawrence,Yufit, Dmitry S.,Sandford, Graham
, p. 3872 - 3878 (2020/06/09)
Fluorinated acyl-Meldrum's acid derivatives were synthesized by electrophilic fluorination of appropriate phenacyl Meldrum's acid substrates using Selectfluor. Reactions with water, ethanol, Grignard, and alkynyllithium reagents gave rise to the correspon
Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation
Zhang, Rui,Ni, Chuanfa,He, Zhengbiao,Hu, Jinbo
, p. 166 - 172 (2017/09/18)
Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.
Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation
Wu, Shu-Wei,Liu, Feng
, p. 3642 - 3645 (2016/08/16)
An efficient and mild fluorination of vinyl azides for the synthesis of α-fluoroketones is described. The mechanistic studies indicated that a single-electron transfer (SET) and a subsequent fluorine atom transfer process could be involved in the reaction.
Synthesis of α-Fluoroketones by Insertion of HF into a Gold Carbene
Zeng, Xiaojun,Liu, Shiwen,Shi, Zhenyu,Liu, Guangchang,Xu, Bo
supporting information, p. 10032 - 10036 (2016/08/16)
Reported is an efficient synthesis of α-fluoroketones by insertion of hydrogen fluoride (HF) into the gold carbene intermediate, generated from a cationic gold catalyzed addition of N-oxides to alkynes. This method results in excellent chemical yields for a wide range of alkyne substrates and demonstrates good functional-group tolerance.
Palladium-catalyzed direct mono-α-arylation of α-fluoroketones with aryl halides or phenyl triflate
Zhou, Jun,Fang, Xiang,Shao, Tongle,Yang, Xueyan,Wu, Fanhong
supporting information, p. 54 - 62 (2016/10/05)
A palladium catalyzed Negishi-type α-arylation of α-fluoroketones with electron-rich and electron-deficient aryl halides or phenyl triflate has been developed. This direct mono-α-arylation method generate a variety of ternary α-aryl-α-monofluoroketones easily in good to excellent yields using XPhos as ligand and Cs2CO3as mild base.
Catalytic Promiscuity of Transaminases: Preparation of Enantioenriched β-Fluoroamines by Formal Tandem Hydrodefluorination/Deamination
Cuetos, Aníbal,García-Ramos, Marina,Fischereder, Eva-Maria,Díaz-Rodríguez, Alba,Grogan, Gideon,Gotor, Vicente,Kroutil, Wolfgang,Lavandera, Iván
supporting information, p. 3144 - 3147 (2016/03/12)
Transaminases are valuable enzymes for industrial biocatalysis and enable the preparation of optically pure amines. For these transformations they require either an amine donor (amination of ketones) or an amine acceptor (deamination of racemic amines). Herein transaminases are shown to react with aromatic β-fluoroamines, thus leading to simultaneous enantioselective dehalogenation and deamination to form the corresponding acetophenone derivatives in the absence of an amine acceptor. A series of racemic β-fluoroamines was resolved in a kinetic resolution by tandem hydrodefluorination/deamination, thus giving the corresponding amines with up to greater than 99 % ee. This protocol is the first example of exploiting the catalytic promiscuity of transaminases as a tool for novel transformations.
One-Pot Synthesis of α-Fluoroketones and 3-Fluoro-2,4-diaryl-furans from Trifluoromethyl β-Diketones via Decarboxylation
Shao, Tongle,Fang, Xiang,Yang, Xueyan
supporting information, p. 1835 - 1840 (2015/08/06)
A facile and mild one-pot protocol via decarboxylation of trifluoromethyl β-diketones has been developed for the construction of α-fluoroketones and 3-fluoro-2,4-diarylfurans which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.
Metal-free, efficient oxyfluorination of olefins for the synthesis of α-fluoroketones
Yang, Qiang,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
supporting information, p. 3460 - 3463 (2014/07/21)
A novel oxyfluorination of olefin reactions has been developed. The reactions involve a metal-free and green catalytic system for the synthesis of α-fluoroketones which is an important building block for organic synthesis. Moreover, this reaction system exhibits great functional group tolerance.
