Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• equivalents to react with various nucleophilic reagents [90]. In 2014, Heimgartner et al. first developed the condensation reaction of a commercially available fluoral hemiacetal with acylhydrazides to yield trifluoromethylated acylhydrazones, and these fluorinated compounds underwent heterocyclization

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

• Greta Utecht-Jarzyńska,
• Karolina Nagła,
• Grzegorz Mlostoń,
• Heinz Heimgartner,
• Marcin Palusiak and
• Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

• bromination of the corresponding trifluoroacetaldehyde hydrazones in dry DMF at room temperature as described in an earlier publication [21]. The latter arylhydrazones were obtained according to a general literature protocol by condensation of aqueous fluoral hydrate (≈75% in H2O) with commercially available

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

• Tatsuhiro Uchikura,
• Nanami Kamiyama,
• Taisuke Ishikawa and
• Takahiko Akiyama

Beilstein J. Org. Chem. 2020, 16, 2442–2447, doi:10.3762/bjoc.16.198

• ][16][17][18][19][20][21]. For example, R3SiCF3, a fluoral derivative, and trifluoroacetates were employed as precursors of CuCF3 species for the catalytic trifluoromethylation of iodoarenes (Figure 1a) and the development of novel types of trifluoromethylating reagents is still desired. We have

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

• Yaochun Xu,
• Isabelle Correia,
• Tap Ha-Duong,
• Nadjib Kihal,
• Jean-Louis Soulier,
• Julia Kaffy,
• Benoît Crousse,
• Olivier Lequin and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276

• compounds. Additional NMR data, computational methods and additional figures and tables. Experimental procedure for fluorescence-detected ThT binding assay and representative curves of ThT fluorescence assays. Acknowledgements Central Glass Co. Ltd. is gratefully acknowledged for kindly providing fluoral

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

• Matthias Wünsch,
• David Schröder,
• Tanja Fröhr,
• Lisa Teichmann,
• Sebastian Hedwig,
• Nils Janson,
• Clara Belu,
• Jasmin Simon,
• Shari Heidemeyer,
• Philipp Holtkamp,
• Jens Rudlof,
• Lennard Klemme,
• Alessa Hinzmann,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240

• -Sulfinyl propargylamine 7k was prepared, following approach II under varying conditions (Table 2). Fluoral hydrate was dehydrated with concentrated sulfuric acid to give trifluoroacetaldehyde by distillation [93]. The reaction of trifluoroacetaldehyde with tert-butyl sulfinamide (S)-1 in the presence of

• hardly depend on the stoichiometry. In the conversion of highly reactive sulfinylimines like 5k, best results were obtained in the absence of a Lewis acid. Analogous investigations with chloral hydrate instead of fluoral hydrate showed that the trichloromethylimine 5l also forms a hemiaminal 8l upon

Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

• Tsuyuka Sugiishi,
• Hideki Amii,
• Kohsuke Aikawa and
• Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

• fluoroalkylated aromatics. Keywords: β-carbon elimination; carbon–carbon bond cleavage; decarboxylation; tetrahedral intermediate; trifluoroacetate; fluoral; trifluoromethylation; Introduction Organofluorine compounds attract attention because of their applicability in various fields, such as medicine

• hemiaminals derived from fluoral (CF3C(OSiMe3)NR2), can generate CnF2n+1Cu via carbon–carbon bond cleavage. Herein we focus on Cu-mediated perfluoroalkylation reactions through which carbon dioxide, the esters, or the N-formylamines are eliminated from the perfluoroalkyl reagents. Review Decarboxylation of

• − sources for perfluoroalkylation reactions. Furthermore, CF3Cu and C2F5Cu were utilized for oxidative perfluoroalkylation reactions of arylboronic acids [44][45] (Scheme 13). Copper-catalyzed group transfer from fluoral derivatives Catalytic systems in organic synthesis are desirable from an

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

• fluoral and morpholine, following the procedure described by B. R. Langlois et al. [77] Moderate to good yields were observed when the reaction was carried out in diglyme with cesium fluoride as a base (Table 14). More recently, compounds derived from trifluoroacetic acid appeared to be a cheap and

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

• Raoni S. B. Gonçalves,
• Michael Dos Santos,
• Guillaume Bernadat,
• Danièle Bonnet-Delpon and
• Benoit Crousse

Beilstein J. Org. Chem. 2013, 9, 2387–2394, doi:10.3762/bjoc.9.275

• Marie Curie program, the Farmaguinhos/FioCruz, and PGQu for financial support. Central Glass Co. Ltd. is gratefully acknowledged for kindly providing fluoral hydrate and HFIP, as well as the IT department from Université Paris-Sud for providing computing resources. The authors would like thank M’bokeno

Synthesis of new triazole- based trifluoromethyl scaffolds

• Michela Martinelli,
• Thierry Milcent,
• Sandrine Ongeri and
• Benoit Crousse

Beilstein J. Org. Chem. 2008, 4, No. 19, doi:10.3762/bjoc.4.19

• spectroscopic data of 2a-i and 4. Acknowledgements Claire Troufflard is gratefully acknowledged for NMR experiments. Central Glass is thanked for kind gift of fluoral hydrate and DSM company for donation of (R)-phenylglycine. We thank the European Community for the financial support (Marie Curie Early Stage