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

Regioselective cobalt(II)-catalyzed [2 + 3] cycloaddition reaction of fluoroalkylated alkynes with 2-formylphenylboronic acids: easy access to 2-fluoroalkylated indenols

• Tatsuya Kumon,
• Miroku Shimada,
• Jianyan Wu,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 2193–2200, doi:10.3762/bjoc.16.184

• determined by 19F NMR spectroscopy. The values in parentheses are the isolated yield of 3. aAtropisomers of 3fA and 5fA were detected. b3.0 equiv of 2 were used. cThe reaction was carried out using 3.0 equiv of 2 in the presence of 20 mol % each of Co(acac)2·2H2O and dppp at 110 °C in a sealed tube

• . Synthesis of the fluoroalkylated indenone 6 and the indanone 7 from the indenol 3aA. The yields were determined by 19F NMR spectroscopy. The values in parentheses are the isolated yields. Stereochemical assignment of 5aA and 7 based on NMR techniques. The cross-peaks were observed through HMBC measurements

• . Proposed reaction mechanism. Screening for the reaction conditions of the cobalt-catalyzed [2 + 3] cycloaddition using the fluoroalkylated alkyne 1a and 2-formylphenylboronic acid (2A). Supporting Information Supporting Information File 454: Experimental procedures, characterization data (1H, 13C, 19F NMR

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• , decreases the environmental impact, and has new modes of action. In analytical chemistry, fluorine nuclei (19F) are ideal for quantitative integration in NMR spectroscopy, comparable to 1H NMR spectroscopy [25][26]. In contrast to 13C signals, fluorine signals are well-resolved, and the nuclear spin of

Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups

• Benjamin Jeffries,
• Zhong Wang,
• Robert I. Troup,
• Anaïs Goupille,
• Jean-Yves Le Questel,
• Charlene Fallan,
• James S. Scott,
• Elisabetta Chiarparin,
• Jérôme Graton and
• Bruno Linclau

Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182

• fluorinated isobutanol, cyclopropylmethanol and 3-oxetanylmethanol derivatives are given in Figure 5. They were measured by a 19F NMR-based method developed by our group [22][27], which is suitable for measuring the octanol/water partition coefficients P of (fluorinated) non-UV active substrates. As expected

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

• Thomas Schneider,
• Michael Keim,
• Bianca Seitz and
• Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

• °C, 19F NMR monitoring of the reaction’s progress indicated the appearance of a second product beside the 1,4-cyclohexadien-1-iminium salt 4-Ch. Further investigations revealed that the new product was the dihydrofluorene 7, resulting from 4-Ch by an intramolecular electrophilic aromatic substitution

• reaction of propyn-1-iminium salt 1a with styrene in acetonitrile was considered first and was monitored by 19F NMR spectroscopy. Whereas no reaction appeared to occur at room temperature, a slow transformation into two fluorine-containing products was observed at 70 °C, which after neutralization and work

• interest to know whether it would react with propyn-1-iminium salts 1 as a styrene or a 1,3-diene. With 3-(4-bromophenyl)propyn-1-iminium salt 1c in acetonitrile, no reaction was observed at 20 °C, but within two hours at 45 °C, an unclean reaction took place, which became evident by a multitude of 19F NMR

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

• of 0 °C instead of 20 °C, for 30 min, complete conversion was achieved and the three products E,Z-9 and 10 were present in a 62:8:26 ratio as determined by 19F NMR, the remaining 4% being attributed to acetylated analogues of 9 (Table 3, entry 1). After purification, two products were obtained as a

• heterocyclic ether 10, the addition of TBAB as a bromide source was explored. To our delight, after 30 min at 0 °C, the crude 19F NMR showed that only 4% of 10 and 96% of 9 as an 84:16 E/Z mixture had formed (Table 3, entry 2). Separation of the two E/Z isomers proved challenging by column chromatography and a

• ) and CSA (2 equiv) an 84% conversion into mainly brominated lactone 15 (79%) with traces of hydroxylated lactone 14, and of bromoalkene Z-13 was determined by crude 19F NMR. The remaining 8% appeared to be the β-chloromethyllactone 19 (see Scheme 7 below), an analogue of 15 as determined by NMR

Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines

• Vladimir Kubyshkin

Beilstein J. Org. Chem. 2020, 16, 1837–1852, doi:10.3762/bjoc.16.151

• [49][50]. The presence of a fluorine-rich group in the structure is also beneficial for the NMR studies based on the detection of the 19F nucleus [51][52][53]. Limited attention has been given to the polarity effects in the proline analogues though. Few studies reported peptides containing proline

• analogues in complex biological systems such as peptides and proteins, especially in 19F NMR labelling, where fluorinated prolines can serve as spectroscopic probes. Potential areas for the application of fluorinated prolines are numerous, and include the design of molecular recognition systems [101

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

• compounds [8][9]. The former takes advantage of the superb properties of the 18F-radioisotope as positron emitter (t1/2 = 109 min, 97% β+ emission), while the latter benefits from the excellent performance of the 19F isotope in NMR (100% natural abundance, high sensitivity, lack of endogenous background

• -aldol reaction affording the final product (Scheme 34). This mechanism was experimentally supported by the beneficial effect of water and the observation of HF-loss by 19F NMR. The catalytic version of this process was also studied. The best results in terms of efficiency and stereoselectivity were

Fluorohydration of alkynes via I(I)/I(III) catalysis

• Jessica Neufeld,
• Constantin G. Daniliuc and
• Ryan Gilmour

Beilstein J. Org. Chem. 2020, 16, 1627–1635, doi:10.3762/bjoc.16.135

• organocatalyst, Selectfluor® was employed as the terminal oxidant, and an amine/HF complex enlisted as the fluoride source (please see Supporting Information File 1 for full details). The reaction was performed in CHCl3 at ambient temperature and the crude reaction mixtures were analysed by 19F NMR spectroscopy

• , carbonyl and alkynyl group are optimally preorganised with a C5 linker. With this in mind, the amide derivatives 12 and 13 were exposed to the standard reaction conditions. Curiously, the reactions were extremely ineffective yielding the respective α-fluoroketones in only 15% yield as determined by 19F NMR

• spectroscopical yields determined by 19F NMR analysis of the crude reaction mixtures using ethyl fluoroacetate as an internal standard. (A) Hammett plot varying the para-substitution on the alkyne (ρ ≈ 0). (B) Hammett plot varying the para-substitution on the catalyst (ρ < 0). An overview of the I(I)/I(III

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

• Alyn T. Davies,
• Mark D. Greenhalgh,
• Alexandra M. Z. Slawin and
• Andrew D. Smith

Beilstein J. Org. Chem. 2020, 16, 1572–1578, doi:10.3762/bjoc.16.129

• : Experimental procedures, product characterization data (mp, NMR, IR, HRMS, [α]D, HPLC), and spectra (1H, 13C, and 19F NMR, HPLC). Supporting Information File 336: Crystallographic details for 12. Acknowledgements We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. Funding We thank

Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers

• Vyacheslav I. Supranovich,
• Vitalij V. Levin and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 1550–1553, doi:10.3762/bjoc.16.126

• analyzed by 19F NMR spectroscopy. A series of typical photocatalysts (for example, iridium catalysts) were ineffective in promoting the reaction. Rewardingly, a gold catalyst, [AuCl(μ-dppm)]2 [25][26][27], provided reasonable yields of 3a after one day of irradiation along with a full conversion of the

• . Yield determined by 19F NMR spectroscopy using an internal standard. Proposed mechanism of the fluoroalkylation reaction. Supporting Information Supporting Information File 332: Full experimental details, compound characterization, and copies of NMR spectra.

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125