135359-29-4Relevant articles and documents
α-Fluorination of carbonyls with nucleophilic fluorine
Adler, Pauline,Teskey, Christopher J.,Kaiser, Daniel,Holy, Marion,Sitte, Harald H.,Maulide, Nuno
, p. 329 - 334 (2019)
Given the unique properties of fluorine, and the ability of fluorination to change the properties of organic molecules, there is significant interest from medicinal chemists in innovative methodologies that enable the synthesis of new fluorinated motifs. State-of-the-art syntheses of α-fluorinated carbonyl compounds invariably rely on electrophilic fluorinating agents, which can be strongly oxidizing and difficult to handle. Here we show that reversing the polarity of the enolate partner to that of an enolonium enables nucleophilic fluorinating agents to be used for direct chemoselective α-C–H-fluorination of amides. Reduction of these products enables facile access to β-fluorinated amines and the value of this methodology is shown by the easy preparation of a number of fluorinated analogues of drugs and agrochemicals. A fluorinated analogue of citalopram, a marketed antidepressant drug, is presented as an example of the preserved biological activity after fluorination.
Deoxyfluorination of alcohols with aryl fluorosulfonates
Fei, Zhongbo,Hu, Jinbo,Li, Wei,Liu, Qinghe,Ni, Chuanfa,Wang, Xiu,Zhou, Min
supporting information, p. 8170 - 8173 (2021/08/23)
Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.
Enantioselective Suzuki cross-couplings of unactivated 1-fluoro-1-haloalkanes: Synthesis of chiral β-, γ-, δ-, and ε-fluoroalkanes
Jiang, Xiaojian,Gandelman, Mark
supporting information, p. 2542 - 2547 (2015/03/04)
The incorporation of fluorine atom into a stereogenic center is a highly challenging transformation with current methodologies offering access mainly to chiral α- and β-fluoroalkanes. In this article, the development of a novel general approach to constru