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U. Cependant and . Large-excès-d, arène est utilisé, la réaction est lente et la régiosélectivité est moyenne à partir d'arènes monosubstitués. Bräse a également réalisé la trifluorométhylation de triazènes à partir de trifluorométhyle d'argent, mais ce dernier est généré, p.576

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. Di, Prepared according to general procedure B from p-tolyl bromide (855 mg, 5 mmol) and ethyl chloroformate (0.20 mL, 2 mmol) Purification on silica gel with petroleum ether-ethyl acetate (25-20:1) afforded the title compound in 92% (389 mg) yield as a pale pink powder, ). 13 C- NMR (75 MHz, pp.15-29

. Bis, tert-butyl)phenyl)methanone C 21 H 26 O (CAS: 15796-82-4): Prepared according to general procedure B from 4-tert-butyl-1-bromobenzene (0

. Hz, 38 (s, 18H) 13 C-NMR (75 MHz, CDCl 3 ) ?/ppm: 196, HRMS (EI+) (C 21 H 26 O): calculated m, pp.294-294, 1984.

. Bis, methylthio)phenyl)methanone C 15 H 14 OS 2 (CAS: 63084-99-1): Prepared according to general procedure B from 4-bromothioanisole (1.016 g, 5 mmol

4. Hz, 53 (s, 6H) 13 C-NMR (75 MHz, CDCl 3 ) ?/ppm: 194

M. Dekan, M. W. Mobli, E. Pennington, E. Fung, P. F. Nemeth et al., Total Synthesis of Human Hepcidin through Regioselective Disulfide-Bond Formation by using the Safety-Catch Cysteine Protecting Group 4,4???-Dimethylsulfinylbenzhydryl, Angewandte Chemie International Edition, vol.15, issue.11, pp.2931-2934, 2014.
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. Hz, 36 (t, J = 7.2 Hz, 6H) 13 C-NMR (75 MHz, CDCl 3 ) ?/ppm: 195, pp.4-36

. Bis, C 13 H 8 Cl 2 O (CAS: 90-98-2): The arylzinc derivative was prepared according to general procedure C from 1-bromo-4-chlorobenzene (957 mg, 5 mmol) It was obtained in 90% GC yield (4.5 mmol)

2. Hz, CDCl 3 ) ?/ppm: 193 (q, J = 272 Hz). 19 F- NMR (282 MHz, CDCl 3 , bis(trifluoromethane)sulfonimide as external reference) ?/ppm: -62, Hz, 2H). 13 C-NMR (75 MHz HRMS (EI+), pp.71-318

. Bis, CAS: 13102-33-5): The arylzinc derivative was prepared according to general procedure C from 2-bromoanisole (0.62 mL, 5 mmol) It was obtained in 79% GC yield (3.95 mmol), pp.15-29

. Hz, 91 (d, J = 8.3 Hz, 2H). 13 C-NMR (75 MHz, CDCl 3 ) ?/ppm: 195

J. =. Ddd, Purification on silica gel with petroleum ether-ethyl acetate (15-12:1) afforded the title compound in 53% (290 mg) yield as a white powder. 1 H-NMR (300 MHz, CDCl 3 ) ?/ppm: 8.45 (dd, J = 1.5, 1.3 Hz, and ethyl chloroformate (0.17 mL, 1.68 mmol) was then added to the reaction mixture (q, J = 7.1 Hz, 4H), 1.40 (t, J = 7.1 Hz, 6H). 13 C-NMR (75 MHz, pp.29-61, 1998.

F. D. Wang, H. Y. Liu, A. D. Tu, and . Zhang, One-Pot Synthesis of Diarylmethanones through Palladium-Catalyzed Sequential Coupling and Aerobic Oxidation of Aryl Bromides with Acetophenone as a Latent Carbonyl Donor, The Journal of Organic Chemistry, vol.79, issue.14, pp.6554-6562, 2014.
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. Bis, -methylphenyl)methanone C 15 H 12 F 2 O: The arylzinc derivative was prepared according to general procedure C from 2-bromo-4-fluorotoluene (0.62 mL, 5 mmol) It was obtained in 95% GC yield (4.75 mmol)
URL : https://hal.archives-ouvertes.fr/halshs-00459328

J. Hzd, 4 Hz), 19.96. 19 F-NMR (282 MHz, CDCl 3 , bis(trifluoromethane)sulfonimide as external reference) ?/ppm: -116 HRMS (EI+) (C 15 H 12 F 2 O): calculated m/z: 246.0856, found: 246.0853. FT-IR (KBr, cm-1): 2930, 1171.

. Di, CAS: 127158-63-8): The arylzinc derivative was prepared according to general procedure C from 3-bromofuran (0.25 mL, 2.78 mmol), pp.9-15

2. Hz, 13 C-NMR (75 MHz, CDCl 3 ) ?/ppm: 191

. Bis, CAS: 90-96-0): (4-methoxyphenyl)zinc bromide was prepared according to general procedure A and was obtained in 60% yield. The reaction medium was then filtered through a syringe filter, and N-formylsaccharin (211 mg, 1 mmol, 1 equiv.) was added to the filtered solution (3.3 mL, 2.5 equiv. of arylzinc bromide) The reaction was stirred at room temperature and followed by GC on idolised aliquots, until (4-methoxyphenyl)zinc bromide was consumed (1 hour) Aqueous hydrochloric acid (1M, 10 mL) was then added to the reaction mixture. The phases were separated, and the aqueous phase was extracted with dichloromethane (3 x 10 mL) The combined organic phases were washed with a saturated solution of NaCl, pp.15-29

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. Hz, 86 (s, 3H), 1.41 (t, J = 7.1 Hz, 3H) 13 C-NMR (75 MHz, CDCl 3 ) ?/ppm: 166

. Hz, bis(trifluoromethane)sulfonimide as external reference) ?/ppm: -62, p.595

Z. X. Wu and . Wang, P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides, Organic & Biomolecular Chemistry, vol.135, issue.33, pp.6414-6424
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4. Hz, 13, C-NMR (75 MHz

S. Sodium and . Sulfurothioate, CAS: 6313-36-6): To a solution of sodium thiosulfate (3.80 g, 24 mmol, 1.2 equiv.) in water (10 mL) and methanol (30 mL) was added benzyl bromide (2.34 mL, 20 mmol, 1 equiv.). The reaction mixture was stirred at 65 °C for 4 h, then cooled to room temperature and concentrated under pressure to remove water and methanol. The reaction mixture was dissolved in methanol (100 mL), heated to 50 °C and filtrated. The filtrate was then concentrated to give the title, 77% (5.49 g, 77 wt.% purity by assay) yield as a white solid. 1 H-NMR (300 MHz, D 2 O): ?/ppm

S. Sodium, CAS: 1561023-51-5): To a solution of sodium thiosulfate (2, pp.3-7

F. González, J. P. Brand, and J. Waser, Ethynyl-1,2-benziodoxol-3(1???H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters, Chemistry - A European Journal, vol.11, issue.31, pp.9457-9461, 2010.
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1. Hz, 83 (s, 3H) 13 C-NMR (75 MHz, CDCl 3 ): ?/ppm: 154, p.89

2. Hz, 77 (s, 3H) 13 C-NMR (75 MHz CDCl 3 ): ?/ppm: 156.21 (d, J = 2, 128.89 (d, J = 2.2 Hz), 126.00 (d, J = 2.3 Hz), 122.22 (d, J = 2.3 Hz), 53.77 (d, J = 2.4 Hz). HRMS (EI+), pp.167-0582

. Methoxy, (trifluoromethyl)sulfinyl)benzene C 8 H 7 F 3 O 2 S (CAS: 32916-20-4): (4-Methoxyphenyl)zinc bromide was prepared according to general procedure A. It was obtained in 62% GC yield (3.1 mmol) and the arylzinc solution was then filtrated to remove excess of zinc, Trifluoromethyl(thio)silver (540 mg, pp.4-58

R. Y. Tang, P. Zhong, and Q. L. Lin, Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid, Journal of Fluorine Chemistry, vol.128, issue.6, pp.636-640, 2007.
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