Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

• Yukiko Karuo,
• Keita Hirata,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

• fact, several inhibitors of the β-site amyloyd β A4 precursor protein cleaving enzyme (BACE1), which is involved in the production of β-amyloid, and fluoroalkene analogs of dipeptidyl peptidase-4 inhibitors have previously been reported [2][3]. These inhibitors possess higher drug efficacies than their

• -coupling proceeded to produce fluoroalkene 2a in 50% yield (Table 1, entry 1). Increasing the amount of 4a to 2.0 equiv and decreasing the amount of palladium diacetate to 5 mol % improved the reaction yield (Table 1, entry 2). When the reaction mixture was heated to 60 °C or reflux conditions, 2a could be

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

• Yukiko Karuo,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

• (s, 1F), −78.4 (s, 1F); EIMS m/z: 268, 270 [M]+; HREIMS: [M]+ calcd for C13H14ClFSi, 268.0486, 270.0457; found, 268.0490, 270.0452. Medicines containing a difluoromethylene group. Fluoroalkene analogs of some drugs. Reaction of phenol with polyfluoroalkanes. Proposed mechanism. Sonogashira cross

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

• Clément Q. Fontenelle,
• Thibault Thierry,
• Romain Laporte,
• Emmanuel Pfund and
• Thierry Lequeux

Beilstein J. Org. Chem. 2020, 16, 1936–1946, doi:10.3762/bjoc.16.160

• conformational changes [11][12][13]. For the latter, nucleoside analogues (Figure 2, VI) containing a trans-butenyl moiety where the endocyclic C–O bond was replaced by a C=C bond are recognized by kinases as dUMP surrogate (V) [11]. However, there is no existing data for the corresponding fluoroalkene (VII), as

• hydrogen-bond accepting capacity with proteins or enzymes would be restored [14]. The synthesis of fluoroalkene precursors of modified acyclonucleosides (VIII) has been explored by Choi, and more recently by us [15][16][17]. Nevertheless, it was reported that no antiviral activity for compounds of series

Pauson–Khand reaction of fluorinated compounds

• Jorge Escorihuela,
• Daniel M. Sedgwick,
• Alberto Llobat,
• Mercedes Medio-Simón,
• Pablo Barrio and
• Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

• which they detailed the Markovnikov hydrofluorination of alkynes using HF.DMPU coupled with a gold catalyst [60]. Accordingly, the appropriate propargylmalonate derivatives were fluorinated to give fluoroalkene intermediates, which were then converted into malonate-based enynes 37 (Z = CO2R) through a

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

• Myriam Drouin and
• Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

• of the geometry of the fluoroalkene (i.e., Z vs E) was important. Finally, as the monofluoroalkene is of interest in medicinal chemistry as a non-hydrolyzable peptide bond isostere, some applications have been presented. Selected amide bond isosteres. Monofluoroalkene as an amide bond isostere

Computational study of productive and non-productive cycles in fluoroalkene metathesis

• Markéta Rybáčková,
• Jan Hošek,
• Ondřej Šimůnek,
• Viola Kolaříková and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2015, 11, 2150–2157, doi:10.3762/bjoc.11.232

• . Keywords: alkene metathesis; computation; DFT; fluoroalkene; mechanism; non-productive cycle; productive cycle; Introduction Over the course of the last 20 years, alkene metathesis catalysed with homogeneous transitition metal-based precatalysts evolved into a valuable tool for organic synthetic chemists

• ] and the analogous reaction of 1-fluoroalkene formed a fluoromethylene-containing complex with low catalytic activity [32][33]. Up to now, the only metathesis which included tetrafluoroethene and its analogues has been reported in a patent [34], describing the disproportionation of perfluoroalkenes and

The vicinal difluoro motif: The synthesis and conformation of erythro- and threo- diastereoisomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives

• David O'Hagan,
• Henry S. Rzepa,
• Martin Schüler and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2006, 2, No. 19, doi:10.1186/1860-5397-2-19

• obtained after a dehydrobromination reaction. The elimination of hydrogen bromide from such β-fluorobromides had been explored previously, and the reaction proceeds in a stereospecific manner to generate either E or Z fluoroalkene products [20]. Accordingly treatment of 14 with potassium tert-butoxide in a