Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

• Yuta Kabumoto,
• Eiichiro Yoshimoto,
• Bing Xiaohuan,
• Masato Morita,
• Motohiro Yasui,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

• amides in moderate three-step yields. Keywords: amine; chirality transfer; [1,3]-proton shift reaction; tetrafluoroethylene fragment; Introduction A fluorine atom has quite peculiar chemical and physical properties compared to others, and hence changes in molecular properties resulting from the

• with a tetrafluoroethylene fragment exhibit significantly different molecular properties compared to monofluorinated, difluorinated, or trifluoromethylated molecules [8][9]. Therefore, more and more tetrafluoroethylenated molecules having a variety of applications, such as bioactive substances (Figure

• which is being abstracted simultaneously interacts with the carbon possessing the tetrafluoroethylene fragment. At this time, transition states TS1 or TS2 are possible, but the reaction proceeds exclusively through the transition state TS1 to avoid significant steric repulsion between the substituent R

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

• Vyacheslav I. Supranovich,
• Igor A. Dmitriev and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 3104–3108, doi:10.3762/bjoc.16.260

• implies multistep protocols, since two distinct bond-forming reactions are necessary for the cycle formation. While mono- and difluorinated piperidines are well known, tetrafluorinated piperidines are rare [19]. At the same time, the chemistry of compounds containing the tetrafluoroethylene fragment

Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

• Ken Tamamoto,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

• synthetic tool for producing functional molecules with a CF2CF2 fragment. Keywords: acid chlorides; cross-coupling; iodoarenes; tetrafluoroethylene fragment; thermally stable zinc reagent; Introduction Recently, much attention has been paid to organic compounds containing a perfluoroalkylene unit, e.g