Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

• Thierry Milcent,
• Pascal Retailleau,
• Benoit Crousse and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

• intramolecular Michael addition. Preliminary conformational studies on tripeptides including this scaffold in the central position show an extended conformation in solution (NMR) and in the solid state (X-ray). Keywords: fluoroalkyl groups; heterocycles; hydrazino acids; peptides; tetrahydropyridazines

Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

• Youlong Du,
• Haibo Mei,
• Ata Makarem,
• Ramin Javahershenas,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

• organic synthesis, as they can be used as diazo intermediates or carbene precursors for the rapid construction of complex molecules along with the introduction of fluoroalkyl groups [14][15][16]. Although the reaction of trifluorodiazoethane [17][18][19][20][21][22][23][24][25][26][27] as well as α-diazo

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

• Kah Yean Lum,
• Jonathan M. White,
• Daniel J. G. Johnson,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

• recent preliminary SAR study identified that substitution at the C8 position with trifluoromethane and difluoroethane moieties using Diversinate™ chemistry increased the potency of the parent scaffold (compound 2), suggesting the potential of these fluoroalkyl groups for improving the potency of other

• investigations by introduction of fluoroalkyl groups to OSM leads with the aim to probe the SAR of 8-fluoroalkylated triazolopyrazine derivatives and further improve their potency. Based on the existing SAR data for the C3 position of the triazolopyrazine core, substituents with a phenyl ring containing alkyl

• evaluation. The incorporation of fluoroalkyl groups at the C8 position of three OSM leads (4–6) was performed using Diversinate™ chemistry following the previously described method (Scheme 2) [14]. The Diversinate™ reagents used in this study were zinc trifluoromethanesulfinate (TFMS), sodium 1,1

A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines

• Zsanett Benke,
• Attila M. Remete and
• Loránd Kiss

Beilstein J. Org. Chem. 2021, 17, 2051–2066, doi:10.3762/bjoc.17.132

• enhance the pharmacokinetic properties of lead candidates in drug research through the improvement in lipophilicity, absorption, distribution, hydrophobicity and metabolism. Considering the high importance of organofluorine chemistry and that of fluoroalkyl groups in pharmaceutical chemistry, a wide range

• of novel and efficient protocols for the introduction of fluorinated scaffolds or fluoroalkyl groups onto organic molecular entities represent a hot topic in synthetic organic chemistry [45][46][47][48]. In order to prepare a certain fluorinated organic molecule, two common approaches are used: i

Synthesis of aryl 2-bromo-2-chloro-1,1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane

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

Beilstein J. Org. Chem. 2021, 17, 89–96, doi:10.3762/bjoc.17.9

• utility of halothane for the synthesis of aryl gem-difluoroalkyl ethers containing the bromochloromethyl group. Keywords: aryl 1,1-difluoroethyl ether; 1,1-difluoroethene; fluorine compound; halothane; phenol; Introduction Molecules containing fluoroalkyl groups are of interest in pharmaceutical and

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

• 1,7-enynes 34 were prepared in three steps from sulfinylimines derived of o-iodobenzaldehydes. A variety of fluorinated compounds bearing fluorine or fluoroalkyl groups attached to the aryl moieties were efficiently prepared (Scheme 15). In this report, the suitability of enynes bearing CF3

• results may suggest that fluoroalkyl groups behave as bulky substituents rather than as electron-withdrawing ones, perhaps due to the purely inductive nature of the latter [71]. In the same work, the authors described the conjugated addition of several nucleophiles to model substrate 59d (Scheme 33). In

Asymmetric synthesis of CF₂-functionalized aziridines by combined strong Brønsted acid catalysis

• Xing-Fa Tan,
• Fa-Guang Zhang and
• Jun-An Ma

Beilstein J. Org. Chem. 2020, 16, 638–644, doi:10.3762/bjoc.16.60

• or fluoroalkyl groups into three-membered N-heterocycles has emerged as an attractive direction due to the unique fluorine effect in pharmaceuticals and biology [7][8][9][10][11]. In this context, it is not surprising that the syntheses of trifluoromethylaziridines have been pursued from versatile

Formal preparation of regioregular and alternating thiophene–thiophene copolymers bearing different substituents

• Atsunori Mori,
• Keisuke Fujita,
• Chihiro Kubota,
• Toyoko Suzuki,
• Kentaro Okano,
• Takuya Matsumoto,
• Takashi Nishino and
• Masaki Horie

Beilstein J. Org. Chem. 2020, 16, 317–324, doi:10.3762/bjoc.16.31

• nickel-catalyzed deprotonative polymerizations. The introduction of oligosiloxanes as side chains improved the solubility in organic solvents, and copolymer components involving less soluble functional groups, such as short alkyl chains or fluoroalkyl groups, could be incorporated into the alternating

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

• Masanori Inaba,
• Tatsuya Sakai,
• Shun Shinada,
• Tsuyuka Sugiishi,
• Yuta Nishina,
• Norio Shibata and
• Hideki Amii

Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12

• considerable importance in chemistry [26][27][28][29][30][31][32]. Enantioselective fluoroalkylation/lactonization reactions are worth investigating since a new stereogenic carbon center next to the fluoroalkyl groups is generated in products 1. To the best of our knowledge, only one successful example of an

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• ; trifluoromethylation; Introduction The fluorine atom has a strong electronegativity and a small atomic radius, and the incorporation of fluoroalkyl groups into molecules imparts a variety of features. The trifluoromethyl group, as the most significant common used fluoroalkyl group, could improve molecular properties

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

• drugs contain fluorine atoms or fluoroalkyl groups, representing 150 fluorinated molecules, and this trend is expected to increase to about 30% in the early future as a new generation of fluorinated compounds is currently in Phase II−III clinical trials [1]. In parallel, pharmaceutical peptides are

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• ][31][32], the trifluoromethylthio anion [29] or electrophilic perfluoroalkylating agents [33]. Others are devoted to particular methods such as trifluoromethylation initiated by sodium dithionite [34] or the electrochemical introduction of fluoroalkyl groups in organic molecules [35]. Moreover, many

Chemical aminoacylation of tRNAs with fluorinated amino acids for in vitro protein mutagenesis

• Shijie Ye,
• Allison Ann Berger,
• Dominique Petzold,
• Oliver Reimann,
• Benjamin Matt and
• Beate Koksch

Beilstein J. Org. Chem. 2010, 6, No. 40, doi:10.3762/bjoc.6.40

• hydrophobic amino acids have been incorporated into the hydrophobic core of peptides, oligomers and proteins, leading to a significant increase in the thermal stability of the structure [12][13][14][15]. The introduction of fluoroalkyl groups into proteins can also enhance the hydrophobicity of the molecule

Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates

• Jun Xu,
• Xiao-Long Qiu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2008, 4, No. 18, doi:10.3762/bjoc.4.18

• fluoroalkyl groups would alter the regioselectivities of acyclic allylic alkylation compared with their non-fluorinated counterparts [12][13][14][15][16][17], their reactions mostly concerned the Pd-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. To the best of