Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

• Carlos R. Azpilcueta-Nicolas and
• Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

• Z-monofluoroalkene product 136 is achieved through anticoplanar elimination of fluoride. Shuhua Li and co-workers reported the generation of alkyl radicals from NHPI esters, mediated by a pyridine-boryl radical reductant species in the context of alkene hydroalkylation [104] and cross

Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes

• Yajing Zhang,
• Qingshan Tian,
• Guozhu Zhang and
• Dayong Zhang

Beilstein J. Org. Chem. 2020, 16, 3086–3092, doi:10.3762/bjoc.16.258

• H2O or of THF and H2O, instead of DCE and H2O, afforded the monofluoroalkene 2a in only a low yield (Table 1, entries 11 and 12), whereas the product 2a was not obtained when using acetonitrile and H2O or when using DMF (Table 1, entries 13 and 14). Similarly, the desired product was not obtained in

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

• -opening reaction with bromide ions, even in the presence of bulky substituents. Keywords: acyclonucleotide; fluorine; monofluoroalkene; oxetane; selective ring-opening reaction; tetrasubstituted alkene; Introduction The introduction of fluorine atoms into organic compounds is known to modify their

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

• incorporated into peptides, it is normally necessary to first synthesize a dipeptide where the amide bond has been replaced with a monofluoroalkene. In that context, this review will present the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres described since 2007. Some

• applications of those compounds will also be presented. Keywords: dipeptide isosteres; monofluoroalkene-based amide bonds; monofluoroalkenes; peptides; synthesis; Introduction Nowadays, the pharmaceutical industry is interested in the development of new categories of drugs. While small molecules were the

• monofluoroalkene is of particular interest as it possesses many relevant characteristics (Figure 2a). The resonance in the amide generates a double bond character between the carbon of the carbonyl and the nitrogen, which is responsible of the slow rotation around this bond. Furthermore, the negative charge is