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《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(4):1121-1124
The first example of a hypervalent iodine(III)‐mediated oxidative fluorination of alkylsilanes by fluoride ions without the use of transition metals is demonstrated. This reaction is operationally simple, scalable, and proceeds under mild reaction conditions. Mechanistic studies suggest the involvement of a single‐electron transfer resulting from the interaction of an organopentafluorosilicate and aryliodonium difluoride, which were generated in situ from the corresponding alkylsilane and iodosobenzene, respectively, in the presence of fluoride ions. 相似文献
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Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron-Rich Substrates
Sayad Doobary Alexi T. Sedikides Henry P. Caldora Dr. Darren L. Poole Dr. Alastair J. J. Lennox 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(3):1171-1176
Fluorinated alkyl groups are important motifs in bioactive compounds, positively influencing pharmacokinetics, potency and conformation. The oxidative difluorination of alkenes represents an important strategy for their preparation, yet current methods are limited in their alkene-types and tolerance of electron-rich, readily oxidized functionalities, as well as in their safety and scalability. Herein, we report a method for the difluorination of a number of unactivated alkene-types that is tolerant of electron-rich functionality, giving products that are otherwise unattainable. Key to success is the electrochemical generation of a hypervalent iodine mediator using an “ex-cell” approach, which avoids oxidative substrate decomposition. The more sustainable conditions give good to excellent yields in up to decagram scales. 相似文献
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Chuanqi Hou Dr. Pinhong Chen Prof. Dr. Guosheng Liu 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(7):2757-2761
The first asymmetric PdII-catalyzed aminofluorination of unactivated alkenes using chiral quinoline-oxazolines (Quox) as ligands has been developed. This reaction provides easy access to a wide array of enantiomerically enriched β-fluoropiperidines in good yields and with excellent enantioselectivity. Notably, Et4NF⋅3 HF as a readily accessible nucleophilic fluoride source was found to play an essential role in the enantioselective control, and CsOCF3 also acts a key additive to improve the excellent ee value of products. 相似文献
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Woo‐Jin Yoo Junpei Kondo Jos A. Rodríguez‐Santamaría Thanh V. Q. Nguyen Sh Kobayashi 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(20):6844-6847
A facile synthetic procedure for the preparation of α‐trifluoromethyl carboxylic acids and esters was achieved through multicomponent coupling reactions between gem‐difluoroalkenes, cesium fluoride, and carbon dioxide. The products were generated in moderate to excellent yields, and the synthetic utility of this method was demonstrated through the preparation of trifluoromethylated versions of popular nonsteroidal anti‐inflammatory drugs (NSAIDs). 相似文献
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《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(41):12837-12841
We report the use of isolable primary and secondary alkylcarbastannatrane nucleophiles in site‐specific fluorination reactions. These reactions occur without the need for transition metal catalysis or in situ activation of the nucleophile. In the absence of the carbastannatrane backbone, alkyltin nucleophiles exhibit no activity towards fluorination. When enantioenriched alkylcarbastannatranes are employed, fluorination occurs predominately via a stereoinvertive mechanism to generate highly enantioenriched alkyl fluoride compounds. These conditions can also be extended to stereospecific chlorination, bromination, and iodination reactions. 相似文献
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