Total synthesis of ent-pavettamine

• Memory Zimuwandeyi,
• Manuel A. Fernandes,
• Amanda L. Rousseau and
• Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

• the 13C NMR spectrum due to the observed distorted quartet at δ 163.7 for the C=O group displaying 2JCF coupling and a quartet at δ 120.3 with a 1JCF coupling constant of 291 Hz. 19F NMR and HRMS further confirmed the presence of the recovered TFA salt of ent-pavettamine (28). However, attempts to

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

• Vojtěch Hamala,
• Lucie Červenková Šťastná,
• Martin Kurfiřt,
• Petra Cuřínová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

• conversion and debenzylation. The values [Hz] of selected coupling constants. Boldfaced values illustrate the trends discussed in the text. Supporting Information Supporting Information File 89: Experimental procedures and spectral data. Supporting Information File 90: Copies of 1H, 13C, 19F, and 2D NMR

Metal-free glycosylation with glycosyl fluorides in liquid SO₂

• Krista Gulbe,
• Jevgeņija Lugiņina,
• Edijs Jansons,
• Artis Kinens and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 964–976, doi:10.3762/bjoc.17.78

• during the glycosylation with glycosyl fluorides in liquid SO2 is proved by 19F NMR spectroscopy. A sulfur dioxide-assisted glycosylation mechanism that proceeds via solvent separated ion pairs is proposed, whereas the observed α,β-selectivity is substrate-controlled and depends on the thermodynamic

• anomeric ratio observed initially for mannoside 3c (α/β = 82:18, Scheme 1). Finally, we proved the formation of the fluorosulfite species by employing 19F NMR spectroscopy (Figure 1). Glycosylation of the reaction mixture was treated with Et3N to stabilize the possibly formed fluorosulfite anions in form

• of an ammonium salt. The 19F NMR spectra of the water-soluble components was than compared to the standard obtained from the reaction between TBAF and SO2. The peak that corresponds to the FSO2− anion was observed at 38.34 ppm (TFA as an external standard, −76.55 ppm) [77]. Also DFT calculations were

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• ribonucleotide had a high resemblance to the unmodified uridine, allowing it to be used as a probe for RNA structure determination through 19F NMR [211]. This modification led to RNA which was stable and predominantly in the C3'-endo (north) conformation [211], similar to the 2',4'-diF-RNA previously reported by

• , following removal of the 3'-O-acetyl group with NH3/MeOH, some TBDMS transfer to the C3' position is seen [211]. 5'-DMT protection then led to the pre-amidite [211]. 19F NMR results show that not only does this modification allow for discernment between ssRNA and dsRNA, but it also allows for the

• nucleoside preorganization [219]. In 2011, a work detailing the first synthesis of both isomers of 3'-fluoro-modified hexitol nucleic acid (FHNA and Ara-FHNA) (Figure 1I) was published (Scheme 9 and Scheme 10) [221]. The incorporation of fluorine has long been used in siRNA [224], miRNA [225], and for 19F

Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

• Dat Phuc Tran,
• Yuki Sato,
• Yuki Yamamoto,
• Shin-ichi Kawaguchi,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

• BioSpin Ascend 400 spectrometer (162 MHz). 19F NMR spectra were recorded on a Bruker BioSpin Ascend 400 spectrometer (377 MHz). IR spectra were recorded on JASCO FT/IR-680Plus instrument. High-resolution mass spectra (HRMS) were recorded on a Bruker micrOTOF II ESI(+)/TOF instrument. General procedure for

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

• Vladimir Kubyshkin,
• Rebecca Davis and
• Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

• containing fluorine have been particularly well characterized for their use as spectroscopic probes, mainly in 19F NMR applications [12][13][14][15]. It is typical that the incorporation of fluorine into certain molecular fragments changes the local polarity as well as the electronic and conformational

• is usually neglected for further investigations. Structural disturbances are also not welcome in spectroscopic studies of fluorine-labeled proteins by 19F NMR spectroscopy. Effectively, it is much better and easier to study a protein that is properly folded, rather than a protein that is misfolded

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

• Yamato Fujihira,
• Yumeng Liang,
• Makoto Ono,
• Kazuki Hirano,
• Takumi Kagawa and
• Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

• preferential formation of stable tetrahedral species I instead of the CF3 ketones 2 in the reaction mixture. However, all the yields were moderate to good. This fact could be explained by the appearance of hydrate products 4 in the 19F NMR spectrum of the crude reaction mixture [72], while the hydrates 4

• ), and e) our group in this work. Substrate scope of esters 1 for trifluoromethylation by HCF3 under the optimized conditions. aDetermined by 19F NMR of the crude 2 with trifluorotoluene as an internal standard. bIsolated yield. cIsolated yield of gram-scale reaction by using 1 g of substrate. Optimized

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

• Anthony J. Fernandes,
• Armen Panossian,
• Bastien Michelet,
• Agnès Martin-Mingot,
• Frédéric R. Leroux and
• Sébastien Thibaudeau

Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32

• phenomenon is shown by a large downfield shift in the 19F NMR spectrum of 8 compared to the neutral precursor 7. Following these studies on the evaluation of fluorine atom(s) substitution on cation behavior, Olah et al. then investigated the expected destabilizing effect resulting from the presence of

• spectroscopic evidence for the complete ionization of several α-(trifluoromethyl) alcohol precursors 9a–c in a superacidic FSO3H–SbF5–SO2 medium. They also brought experimental 19F NMR variation values up to Δδ = +24.8 ppm (Scheme 3). This suggests a partial stabilization of the cationic center by

• partial stabilization of the cationic center by the phenyl groups. Similarly, Laali et al. observed significant 19F NMR downfield chemical shifts upon the formation of α-(trifluoromethyl)pyrenylcarbenium- and α-(trifluoromethyl)anthracenylcarbenium ions 12a–d from the corresponding carbinols 11a–d (Scheme

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• use of 19F NMR in the broad field of chemical biology [Cobb, S. L.; Murphy, C. D. J. Fluorine Chem. 2009, 130, 132–140] and present here a summary of the literature from the last decade that has the technique as the central method of analysis. The topics covered include the synthesis of new

• fluorinated probes and their incorporation into macromolecules, the application of 19F NMR to monitor protein–protein interactions, protein–ligand interactions, physiologically relevant ions and in the structural analysis of proteins and nucleic acids. The continued relevance of the technique to investigate

• biosynthesis and biodegradation of fluorinated organic compounds is also described. Keywords: biotransformation; chemical biology; fluorine; 19F NMR; probes; protein structure; Introduction Although fluorine is abundant in the environment, it is not a nutrient nor is it a feature of biochemistry for most

Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions

• Jean C. Kazmierczak,
• Roberta Cargnelutti,
• Thiago Barcellos,
• Claudio C. Silveira and
• Ricardo F. Schumacher

Beilstein J. Org. Chem. 2021, 17, 234–244, doi:10.3762/bjoc.17.24

• conditions.a Substrate scope for the synthesis of the α-organylthio esters 3.a Substrate scope for the synthesis of the β-organylthio ketones 4.a Supporting Information Supporting Information File 204: Experimental procedures, characterization data, control experiments, and copies of the 1H, 13C, and 19F NMR

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

• Michael Andresini,
• Leonardo Degannaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20

• )-4-methylbenzene (1a) under batch conditions. Flow cyclization of 1-(1-azidovinyl)-4-methylbenzene (1a). Supporting Information Supporting Information File 110: Description of general methods, general procedures, characterization data for all compounds and copies of 1H,13C,19F, NOESY spectra

Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

• Takashi Yamazaki,
• Yoh Nakajima,
• Minato Iida and
• Tomoko Kawasaki-Takasuka

Beilstein J. Org. Chem. 2021, 17, 132–138, doi:10.3762/bjoc.17.14

• oxidation of the other substrates 1 was performed under similar reaction condition, the results of which are summarized in Table 1. We reported the yield as determined by 19F NMR spectroscopy rather than after purification because of the inherent instability of 2 on silica gel, causing partial decomposition

• . The crude mixture proved to be substantially pure, and thus 2c and 2d afforded appropriate analytical data, including NMR (1H, 13C, and 19F), IR, as well as high-resolution MS data. This process allowed us to obtain the required ynones 2 as long as the residue R was aromatic, while with an aliphatic

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

• information 1H NMR, 13C NMR and 19F NMR spectra were recorded on JEOL ECZ 400S spectrometers. Chemical shifts of 1H NMR are reported in ppm from tetramethylsilane (TMS) as an internal standard. Chemical shifts of 13C NMR are reported in ppm from the center line of the triplet at 77.16 ppm for

• deuteriochloroform. Chemical shifts of 19F NMR are reported in ppm from CFCl3 as an internal standard. All data are reported as follows: chemical shifts, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, sep = septet, br = broad, brd = broad-doublet, m = multiplet), coupling constants (Hz), relative

• ), 7.20–7.31 (m, 5H), 7.35–7.42 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 53.5 (t, J = 41.7 Hz), 119.7 (t, J = 267.1 Hz), 121.8, 126.5, 129.7, 149.7; 19F NMR (376 MHz, CDCl3) δ −77.9 (dd, J = 136.9, 5.2 Hz, 1F), −78.2 (dd, J = 136.9, 5.2 Hz, 1F); EIMS (m/z): 270, 272 [M]+; HRMS–EI (m/z): [M]+ calcd for

Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

• Armin Ariamajd,
• Nils J. Gerwien,
• Benjamin Schwabe,
• Stefan Dix and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2021, 17, 83–88, doi:10.3762/bjoc.17.8

• species with 19F and 1H spectra consistent with the trifluoromethyl thionoester 4a (7% NMR yield, Table 1, entry 1). The formation of both species can be explained by the mechanism shown in Scheme 3 [36]. Nucleophilic attack of the alcohol in the presence of NEt(iPr)2 at the C2-position of the BT reagent

• perfluoroalkylthiolate nucleophiles. Each of the other BT-SRF reagents (1.25 equiv) was reacted with alcohol 2a and NEt(iPr)2 (2 equiv) in MeCN at −40 °C and, after 2 h, the crude mixture was analysed by 1H and 19F NMR. As shown in Table 1, a significant decrease in the nucleophilic perfluoroalkylthiolation efficiency

Amine–borane complex-initiated SF₅Cl radical addition on alkenes and alkynes

• Audrey Gilbert,
• Pauline Langowski,
• Marine Delgado,
• Laurent Chabaud,
• Mathieu Pucheault and
• Jean-François Paquin

Beilstein J. Org. Chem. 2020, 16, 3069–3077, doi:10.3762/bjoc.16.256

• reported. aYield estimated by 19F NMR analysis of the crude mixture using 2-fluoro-4-nitrotoluene as an internal standard. Scope of the Et3B and the DICAB-initiated SF5Cl additions on alkynes. Unless noted otherwise, isolated yields are reported. aYield estimated by 19F NMR analysis of the crude mixture

• Supporting Information File 348: General information, synthetic procedures, additional optimization results, NMR spectra for known compounds (1H, 19F) and full characterization of all new compounds. Funding We acknowledge the financial support of the Natural Sciences and Engineering Research Council of

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD^®/Olah’s reagent under solvent-free conditions

• Yumeng Liang,
• Akihito Taya,
• Zhengyu Zhao,
• Norimichi Saito and
• Norio Shibata

Beilstein J. Org. Chem. 2020, 16, 3052–3058, doi:10.3762/bjoc.16.254

• reaction conditions). The investigation of a range of parameters showed that the best results were achieved by the combination of 3 equiv FLUOLEAD® and 5 equiv nHF·pyridine in solvent-free conditions at 70 °C for 24 h, providing the product 4-(trifluoromethyl)-1,1'-biphenyl (2a) in 99% 19F NMR yield (Table

• mL), and the combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The yield was determined by 19F NMR analysis of the crude mixture by using C6H5OCF3 (40.0 μL, 0.3 mmol, 1.0 equiv) as an internal standard. The residue was purified by silica gel

• by FLUOLEAD®. The substrate scope of acyl fluorides. Reaction conditions: 1 (0.3 mmol), FLUOLEAD® (0.9 mmol, 3.0 equiv) and nHF·pyridine (1.5 mmol, 5.0 equiv) in neat conditions at 70 °C for 24 h. Yields in parentheses were determined by 19F NMR spectroscopy. aAt 100 °C. bUsing 1a (1.0 g, 5.0 mmol

Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate

• Kevin Grollier,
• Alexis Taponard,
• Arnaud De Zordo-Banliat,
• Emmanuel Magnier and
• Thierry Billard

Beilstein J. Org. Chem. 2020, 16, 3032–3037, doi:10.3762/bjoc.16.252

• THF. Then, compound 2a–n (0.4 mmol, 2 equiv) was added followed by TBAI (0.4 mmol, 2 equiv). The tube is then sealed and the reaction mixture stirred at 40 °C for 4 h. The conversion was checked by 19F NMR spectroscopy with PhOCF3 as internal standard. After completion, the reaction mixture was

• concerning the direct nucleophilic trifluoromethylselenolation. The nucleophilic fluoroalkylselenolation of alkyl bromides. Yields were determined by 19F NMR spectroscopy with PhOCF3 as an internal standard and yields of isolated products are shown in parentheses. aWith 1 equiv of electrophile 2. bStarting

Controlled decomposition of SF₆ by electrochemical reduction

• Sébastien Bouvet,
• Bruce Pégot,
• Stéphane Sengmany,
• Erwan Le Gall,
• Eric Léonel,
• Anne-Marie Goncalves and
• Emmanuel Magnier

Beilstein J. Org. Chem. 2020, 16, 2948–2953, doi:10.3762/bjoc.16.244

• hexafluoride dissolved in various organic solvents. After combining an analytical approach of electrochemistry and 19F NMR spectroscopy, we have succeeded in the total consumption of SF6 in an electrochemical cell. Results and Discussion The first step of this work began with the measurement of the solubility

• . The solubility of SF6 was measured, at 20 °C, by 19F NMR with chlorodifluoromethoxybenzene as internal standard probe. The concentration value for DMF was quite low (0.17 g/L) whereas the one for acetonitrile (2.48 g/L) was convenient for further studies. Acetonitrile is a common nonaqueous solvent in

• also monitored by 19F NMR (Figure 5). After 3 hours experience, unidentified side-products were detected by NMR. Identification of these fleeting species as well as their potential reactivity are under current investigation in our laboratory. The left part of Figure 5 clearly demonstrates the total

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

• Danny Lainé,
• Vincent Denavit,
• Olivier Lessard,
• Laurie Carrier,
• Charles-Émile Fecteau,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2020, 16, 2880–2887, doi:10.3762/bjoc.16.237

• reactions were monitored using 19F NMR spectroscopy with 2-fluoro-4-nitrotoluene as internal standard. Fluorodeoxygenation of glucopyranose 2 gave galactose 10 (inversion of configuration), as the only diastereoisomer (Table 1, entry 1). Interestingly, the epimer at C4 (compound 3) provided galactose 10

• , entry 1). To our delight, mannose analogue 14 was formed as the major product (44% yield), along with 21% of the talose analogue 12 and the elimination product 15 in 20% yield, as determined after analysis of the 19F NMR spectra of the crude reaction mixture. Figure 2 shows a representative 19F NMR

• 9 from levoglucosan 1. Typical 19F NMR spectrum (470 MHz, CDCl3) of the crude reaction mixture using Et3N·3HF/Et3N (entry 3 of Table 2). Fluorination at C4 of 1,6-anhydro-2,3-difluorohexopyranose analogues. a) Reactions on triflates 13, 16–18, dipole of C–F bonds are displayed in green arrows; b

Synthesis of purines and adenines containing the hexafluoroisopropyl group

• Viacheslav Petrov,
• Rebecca J. Dooley,
• Alexander A. Marchione,
• Elizabeth L. Diaz,
• Brittany S. Clem and
• William Marshall

Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224

• isomeric products 3a and 3b (Scheme 2). The major isomer 3a was isolated in a pure form, and the structure was confirmed by X-ray diffraction. It should be pointed out that the 19F NMR spectra of the two isomers were very different. While the resonance corresponding to the CH(CF3)2 group in the spectrum of

• in the formation of two regioisomers, 4a and 4b (Scheme 3). In this context, the isomers 4a and 4b were separated by column chromatography (see Experimental section), and the structure of both was established by X-ray diffraction. In the 19F NMR spectra of both isomers 4a and 4b, the resonances

• the compounds 5a and 6a relies solely on NMR data. In both cases, the data were consistent with the structures 5a or 6a, carrying NH2 and CH(CF3)2 groups on the same side of the molecule. Indeed, in the 19F NMR spectra of 5a and 6a, the resonance corresponding to CH(CF3)2 was significantly broadened

A heterobimetallic tetrahedron from a linear platinum(II)-bis(acetylide) metalloligand

• Matthias Hardy,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2020, 16, 2701–2708, doi:10.3762/bjoc.16.220

• recorded on a Bruker Avance I 500 spectrometer. 1H NMR chemical shifts are reported relative to the residual solvent peak and 13C NMR chemical shifts are reported relative to the solvent peak. 19F and 31P NMR chemical shifts are reported relative to external references (CF3COOD in D2O for 19F and D3PO4 for

• 31P). In order to measure 19F and 31P NMR spectra, the NMR tube was equipped with a coaxial insert containing the external standards. 1H NMR data are reported as follows: chemical shift (δ) in ppm, multiplicity (dt = doublet of triplets, m = multiplet), coupling constant (J) in Hertz (Hz), integral

• , CD3CN, 298 K) δ [ppm] 4.66–4.47 (m); 19F NMR (470 MHz, CD3CN, 298 K) δ [ppm] −79.4 (CF3SO3−); DOSY (500 MHz, CD3CN, 298 K, τ = 150 ms): D = 3.33∙10−10 m2/s, dh = 33 Å, rh = 1.65 nm; ESI(+)-MS (CH3CN, M = {C320H432Fe4N24P12Pt6}8+) m/z: 1720.141 [M + 4OTf]4+, 1542.718 [Fe(C52H72N4P2Pt)3]2+, 1433.608 [Fe2

Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles

• Ziyi Li,
• Li Wang,
• Yunqi Huang,
• Haibo Mei,
• Hiroyuki Konno,
• Hiroki Moriwaki,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2020, 16, 2671–2678, doi:10.3762/bjoc.16.217

• ), CH2Cl2 (3 mL), −78 °C, under nitrogen, 2.5 h. Isolated yields of mixture of isomers. Diastereoselectivities were determined by 19F NMR. Large-scale application of the reaction. Removal of the chiral auxiliary. Optimization of reaction conditions.a Supporting Information Supporting Information File 420

Activation of pentafluoropropane isomers at a nanoscopic aluminum chlorofluoride: hydrodefluorination versus dehydrofluorination

• Maëva-Charlotte Kervarec,
• Thomas Braun,
• Mike Ahrens and
• Erhard Kemnitz

Beilstein J. Org. Chem. 2020, 16, 2623–2635, doi:10.3762/bjoc.16.213

• =CHCH2C6D5 (9) and CF3CH=CHC6D5 (8, Scheme 11, middle). In neat silane, 5 and 6 were detected in a ratio of 1:4 (Scheme 11, bottom). Notably, for all conversions (C6D6 and silane, C6D12 and silane, or in neat silane), monitoring of the reaction by 19F NMR spectroscopy led to the observation of the early

• DPX 300 spectrometer. A capillary of trifluorotoluene was employed as an external standard for quantification purposes. The 19F NMR spectra were referenced to PhCF3 (δ = −63.5 ppm) and the chemical shifts in 1H NMR were referenced to residual C6D5H (δ = 7.16 ppm) or C6D11H (δ = 1.38 ppm). Procedure

• mL of HSiEt3 was added using Schlenk techniques to the JYoung NMR tube loaded with ACF. The gases were then condensed using a small glass bulb filled with 0.5 atm of the corresponding gas (0.1 mmol). The reactions were monitored by 1H and 19F NMR spectroscopy. The tubes were kept at 70 °C for 7 days

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

• , hexafluorobenzene was added as an internal standard and the mixture analyzed by 19F NMR spectroscopy for the calculation of the NMR yield. Then, the crude products were purified by preparative TLC to give pure products 3. Trifluoromethylation of aryl halides. Scope of aryl iodides. Yields determined by 19F NMR

• spectroscopy and used ligand is given in parenthesis. Scope of heteroaryl iodides. Yields determined by 19F NMR spectroscopy and used ligand is given in parenthesis. Time course of the trifluoromethylation reaction. Proposed mechanism of the catalytic cycle. Screening for reaction conditionsa. Screening for

Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

• Viktor M. Tkachuk,
• Oleh O. Lukianov,
• Mykhailo V. Vovk,
• Isabelle Gillaizeau and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

• ). Structural determination of compound 3а was performed by IR and 1Н, 13С, and 19F NMR spectroscopy as well as by LCMS and HRMS analysis. Performing the reaction with substrate 1а under the optimum conditions (see Table 1, entry 18), we examined a variety of (het)aryl- and alkenylboronic acids 2b–w as coupling