865075-07-6Relevant academic research and scientific papers
Regio- and chemoselectivity in S- and O- difluoromethylation reactions using diethyl (bromodifluoromethyl)phosphonate
Gershonov, Eytan,Amir, Dafna,Redy-Keisar, Orit,Binyamin, Iris,Yehezkel, Lea,Marciano, Daniele,Drug, Eyal,Fridkin, Gil,Zafrani, Yossi
, (2021/09/08)
The effective difluoromethylations of various S- and O- based- nucleophiles, presenting a wide range of pKa values, using diethyl(bromodifluoromethyl) phosphonate (1) under basic conditions is described. These reactions, which rely on the quantitative generation of difluorocarbene formed through the hydrolysis of 1, were found to be effective only once the starting materials had pKa values of less than ca. 11. Importantly, in cases in which the substrates held two or three nucleophilic centers this feature was successfully implemented to achieve a high chemo- or regioselective difluoromethylation of the center exhibiting the lowest pKa value and the highest polarizability.
Direct Synthesis of N-Difluoromethyl-2-pyridones from Pyridines
Zhou, Sen,Hou, Xiaoya,Yang, Kai,Guo, Minjie,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei
supporting information, p. 6879 - 6887 (2021/05/29)
A novel method for the synthesis of N-difluoromethyl-2-pyridones was described. This protocol enables the synthesis of N-difluoromethyl-2-pyridones from readily available pyridines using mild reaction conditions that are compatible with a wide range of functional groups. The preliminary mechanistic study revealed that N-difluoromethylpyridinium salts were the key intermediates to complete this conversion.
Modulation of the H-Bond Basicity of Functional Groups by α-Fluorine-Containing Functions and its Implications for Lipophilicity and Bioisosterism
Zafrani, Yossi,Parvari, Galit,Amir, Dafna,Ghindes-Azaria, Lee,Elias, Shlomi,Pevzner, Alexander,Fridkin, Gil,Berliner, Anat,Gershonov, Eytan,Eichen, Yoav,Saphier, Sigal,Katalan, Shahaf
, p. 4516 - 4531 (2021/05/07)
Modulation of the H-bond basicity (pKHB) of various functional groups (FGs) by attaching fluorine functions and its impact on lipophilicity and bioisosterism considerations are described. In general, H/F replacement at the α-position to H-bond acceptors l
NHC-catalyzed generation of difluorocarbene and its application to difluoromethylation of oxygen nucleophiles
Fuchibe, Kohei,Koseki, Yuta,Aono, Tatsuya,Sasagawa, Hisashi,Ichikawa, Junji
experimental part, p. 52 - 60 (2012/02/04)
Controlled generation of difluorocarbene was effected by an NHC catalyst under mild conditions starting from trimethylsilyl 2,2-difluoro-2- fluorosulfonylacetate (TFDA). Cyclohexenones and tetralones were treated with TFDA in the presence of catalytic amo
