Trifluoromethylation and Perfluoroalkylation of. Arenes and Heteroarenes in Organic Media

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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information A Vitamin B 12 Derivative Catalyzed Electrochemical Trifluoromethylation and Perfluoroalkylation of Arenes and Heteroarenes in Organic Media Md. Jakir Hossain, a Toshikazu Ono, a,b,c* Kosuke Wakiya, a Yoshio Hisaeda, a,b* a Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka , Japan b Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka , Japan c PRESTO, Japan Science and Technology Agency (JST), Honcho, Kawaguchi, Saitama , Japan 1

2 Experimental section Materials and Measurements. All chemical reagents and solvents used in this study were obtained from commercial sources and used as received unless otherwise stated. Heptamethyl cobyrinate perchlorate (Figure 1(c)) was synthesized by a previously reported method. 1 DMSO-CF 3 was synthesized according to the previous report. 2 The electronic absorption spectra were measured at room temperature using a Hitachi U-3310 spectrophotometer and a 10 mm cell. The 1 H NMR spectra were recorded by a Bruker Avance 300 spectrometer and a JEOL 400 spectrometer at the Centre of Advanced Instrumental Analysis, Kyushu University and the chemical shifts (in ppm) were referenced relative to (CH 3 ) 4 Si, with the residual solvent peak of CDCl 3 at 7.26 ppm. The 1 H NMR spectra was also recorded in C 6 D 6 and referenced to residual C 6 D 6 at 7.16 ppm. The 19 F NMR spectra were recorded by a Bruker Avance 300 spectrometer and a JEOL 400 spectrometer at the Centre of Advanced Instrumental Analysis, Kyushu University, and the chemical shifts (in ppm) were referenced relative to C 6 F 6 at ppm in CDCl 3 and C 6 D 6. The coupling constants, J are reported in Hertz (Hz). EI-MS was performed on a JEOL JMS-700 instrument. ESI-MS was performed on a microtof-qiii mass spectrometer with methanol as the solvent. MALDI-TOF-MS spectra were obtained on Autoflex III (Bruker Daltonics) under the linear/positive mode with dithranol as matrix. Cyclic voltamogram and the controlled potential electrolyses were carried out using a BAS ALS-630C electrochemical analyzer. The gas chromatography-mass spectra (GC- MS) were obtained using a Shimadzu GCMS-QP5050A equipped with a J&W Scientific DB-1 column (length: 30 m; ID: 0.25 mm, film: 0.25 mm) and helium as the carrier gas. For the measurement, the injector and detector temperatures were 250ºC, the oven temperature was initially held at 100ºC for 2 min, then increased to 240ºC at the rate of 10ºC/min. A 200W tungsten lamp was used as the visible light irradiation experiment. After the catalytic reaction, purification of the crude mixtures was performed by preparative TLC and GPC. Gel permeation chromatography (GPC) was carried out by a Japan Analytical Industry Co. Ltd., LC-908 apparatus equipped with a 35 UV-3702 attachment using three connected columns, JAIGEL-1H, 2H, and 2.5 H with a CHCl 3 eluent. The ESR spectra were measured by a Bruker EMX Plus 8/2.7 spectrometer at room temperature. The following abbreviations were used to explain the multiplicities: s = singlet, brs = broad singlet, d = doublet, dd = double doublet, t = triplet, tt = triple triplet, m = multiplet. 2

3 X-ray crystal structural analysis. Single crystals suitable for X-ray structural analysis were obtained by recrystallization using solvent diffusion method. The crystals were mounted on a glass fiber, and used for X-ray diffraction study. Diffraction data were collected with a Bruker SMART APEX CCD diffractometer equipped with graphitemonochromated Mo Kα radiation (λ = Å) from a fine-focus sealed tube operated at 50 kv and 30 ma. The data frames were integrated using SAINT 3 and merged to give a unique dataset for the structure determination. Empirical absorption corrections by SADABS 4 were carried out. The structures were solved by a direct method, and refined by the full-matrix leaset-squares method on all F 2 data using the SHELX suite of programs. 5 Hydrogen atoms were calculated positions and included in the structure factor calculations, but were not refined. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication as CCDC (2 CF 3 ), CCDC (2 C 3 F 7 ), CCDC (2 C 4 F 9 ), CCDC (2 C 8 F 17 ), CCDC (2 C 10 F 21 ), CCDC (4 C 3 F 7 ), CCDC (9 C 4 F 9 ), and CCDC (9 C 8 F 17 ). These data can be obtained free of charge via (or from the Cambridge Crystallogrphic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). 3

4 General procedure of catalytic trifluoromethylation and perfluoroalkylation reaction under electrochemical conditions. Controlled-potential electrolyses were carried out in dry methanol at -0.8 V vs. Ag/AgCl under N 2 atmosphere in an undivided electrolysis cell. The electrolysis cell was equipped with three electrodes; i.e., a platinum mesh cathode, a sacrificial Zn-plate anode, and an Ag/AgCl as a reference electrode. For a typical reaction, a methanol solution of the heptamethyl cobyrinate perchlorate (1) ( M); was dissolved in a methanol solution of 1,3,5-trimethoxybenzene ( M); n-bu 4 ClO 4 (0.1 M); Internal standard C 12 F 10 (decafluorobiphenyl) with stirring and then irradiation with a visible light (>420 nm). Fluoroalkylating reagent (n-c n F 2n+1 I, 9 eq. to substrate) dissolved in methanol was taken into a 5 ml diameter syringe pump and then it was connected to a reaction cell which supplied a constant flow (1 eq. to substrate per 1.0 hour) of fluoroalkylating reagent to the reaction mixture about 9.0 h. N 2 gas was passed over the solution during the measurement to remove O 2 from the reaction system. Syringe pump Light source Reaction cell Figure S1. Experimental setup image of controlled-potential electrolyses. 4

5 Figure S2. GC-MS chart of (a) before and after electrochemical perfluoroalkylation in methanol under (b) -0.8 V vs. Ag/AgCl for 9 h (Entry 2 in Table 1), and (c) -0.9 V vs. Ag/AgCl for 9 h (Entry 3 in Table 1). The results suggested that -0.8 V vs. Ag/AgCl is suitable for performing the catalytic reactions. The by-products were not characterized at this stage. 5

6 (a) g = G (c) H(G) C 3 F 7 N O PBN C 3 F 7 MW: 346 A H = 3.65 G (b) GC-MS PBN C 3 F 7 A N = G OMe C 3 F Fragmentation pattern C 12 F 10 MeO OMe 2 C 3 F 7 Retention time (min) C 3 F 7 m/z H N C 3 F 7 OH MW: 259 MW: 291 Figure S3. (a, b) ESR and GC-MS spectra of PBN C 3 F 7 observed during the electrolysis in methanol after 1h at -0.8 V vs. Ag/AgCl; [1]= ( M); [1,3,5- trimethoxybenzene]= ( M); [PBN]= ( M); [n-bu 4 NClO 4 ]= 0.1 M under N 2. (c) Chemical structure of PBN C 3 F 7 adduct estimated by ESR and GC-MS. 6

7 Estimation of catalyst recovery rate by UV-vis spectra. After the electrochemical perfluoroalkylation in methanol (Entry 2 in Table 2), MALDI-TOF-MS spectra was measured, indicating corrin-type molecule was still present as shown in Figure S5. Moreover, the UV-vis spectrum [Figure S4 (b) (orange line)] indicated that heptamethyl cobyrinate perchlorate (1) possessed the mixture of Co(II) and Co(III) after the reaction. Therefore, we measured the concentration of 1 by addition of cyanide under air to form dicyanoheptamethyl cobyrinate (1-(CN) 2 ) as shown in Figure S4(a). The result indicated that ca. 80 % of 1 was remained after the reaction. (a) (b) Figure S4. Estimation of catalyst recovery rate by UV-vis spectra. 7

8 observed calculated CO 2 CH 3 CO2 CH 3 + N 1036 H 3 CO 2 C CO 2 CH 3 TBA 1 H 3 CO 2 C N N Co II N N H 3 CO 2 C CO 2 CH 3 Figure S5. MALDI-TOF-MS spectra after the catalytic reaction. 8

9 Products data 1,3,5-Trimethoxy-2-(trifluoromethyl)benzene (2 CF 3 ) CF 3 H 3 CO 2 CF 3 Compound 2 CF 3 was prepared according to the general procedure using trifluoromethyl iodide, DMSO-CF 3 I (9 equiv., 540 µl, 5.0x10-2 M) in 56% yield as a white solid. 1 H NMR (300 MHz, CDCl 3 ): δ 6.13 (s, 2H), 3.84 (s, 9H); 19 F NMR (300 MHz, CDCl 3 ): δ (s, 3F); HRMS (ESI, m/z): Cald. for C 10 H 12 F 3 O 3 [M+H] ; found: ,3,5-Trimethoxy-2-(heptafluoropropyl)benzene (2 C 3 F 7 ) C 3 F 7 H 3 CO 2 C 3 F 7 Compound 2 C 3 F 7 was prepared according to the general procedure using heptafluoropropyl iodide, C 3 F 7 I (9 equiv; 324 µl, 5.0x10-2 M) in 84% yield as a white solid. 1 H NMR (300 MHz, CDCl 3 ): δ 6.14 (s, 2H), 3.84 (s, 3H), 3.80 (s, 6H); 19 F NMR (300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (ESI, m/z): Cald. for C 12 H 11 F 7 O 3 Na [M+Na] ; found: ,3,5-Trimethoxy-2-(nonafluorobutyl)benzene (2 C 4 F 9 ) C 4 F 9 H 3 CO 2 C 4 F 9 Compound 2 C 4 F 9 was prepared according to the general procedure using nonafluorobuty iodide, C 4 F 9 I (9 equiv; 387 µl, 5.0x10-2 M) in 75% yield as a white solid. 1 H NMR (300 MHz, CDCl 3 ): δ 6.14 (s, 2H), 3.84 (m, 3H), 3.80 (m, 6H); 19 F NMR (300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F); (t, J = 12.0 Hz, 2F), (m, 2F), (m, 2F); HRMS (ESI, m/z): Cald. for C 13 H 12 F 9 O 3 [M+H] ; found: ,3,5-Trimethoxy-2-(heptadecafluoro-n-octyl)benzene (2 C 8 F 17 ) C 8 F 17 H 3 CO 2 C 8 F 17 Compound 2 C 8 F 17 was prepared according to the general procedure using heptadecafluoro-n-octyl iodide, C 8 F 17 I (9 equiv; 594 µl, 5.0x10-2 M) in 71% yield as a white solid. 1 H NMR (300 MHz, CDCl 3 ): δ 6.15 (s, 2H), 3.84 (s, 3H), 3.81 (s, 6H); 19 F NMR (300 MHz, CDCl 3 ): δ (t,j = 9.0 Hz, 3F); (m, 2F), (m, 8F), (s, 2F), (s, 2F); HRMS (ESI, m/z): Cald. for C 17 H 11 F 17 O 3 Na [M+Na] ; found:

10 1,3,5-Trimethoxy-2-(heneicosafluorodecyl)benzene (2 C 10 F 21 ) C 10 F 21 H 3 CO 2 C 10 F 21 Compound 2 C 10 F 21 was prepared according to the general procedure using heneicosafluorodecyl iodide, C 10 F 21 I (3 equiv; 484 mg, 5.0x10-2 M) in 37% yield as a white solid. 1 H NMR (300 MHz, CDCl 3 ): δ 6.15 (s, 2H), 3.84 (s, 3H), 3.80 (s, 6H); 19 F NMR (300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F); (t, J = 12.0 Hz, 2F), (m, 12F), (brs, 2F), (brs, 2F); HRMS (ESI, m/z): Cald. for C 19 H 11 F 21 O 3 Na [M+ Na] ; found: ,4-Dimethoxy-2-(trifluoromethyl)benzene (3 CF 3 ) CF 3 3 CF 3 Compound 3 CF 3 was prepared according to the general procedure using trifluoromethyl iodide, DMSO-CF 3 I (9 equiv., 549 µl, 5.0x10-2 M) in 20% yield as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ): δ 7.12 (d, J = 3.0 Hz, 1H), 7.01 (dd, J = 9.0, 3.0 Hz, 1H), 6.96 (d, J= 9.0 Hz, 1H), 3.86 (s, 3H), 3.80 (s, 3H); 19 F NMR (300 MHz, CDCl 3 ): δ (s, 3F); HRMS (ESI, m/z): Cald. for C 9 H 9 F 3 O 2 Na [M+Na] ; found: ,4-Dimethoxy-2-(heptafluoropropyl)benzene (3 C 3 F 7 ) C 3 F 7 3 C 3 F 7 Compound 3 C 3 F 7 was prepared according to the general procedure using heptafluoropropyl iodide, C 3 F 7 I (9 equiv., 333 µl, 5.0x10-2 M) in 68% yield as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ): δ (m, 2H), 6.97 (d, J= 9.0 Hz, 1H), 3.82 (m, 3H), 3.80 (m, 3H); 19 F NMR (300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (ESI, m/z): Cald. for C 11 H 10 F 7 O 2 [M+H] ; found: ,4-Dimethoxy-2-(nonafluorobutyl)benzene (3 C 4 F 9 ) C 4 F 9 3 C 4 F 9 Compound 3 C 4 F 9 was prepared according to the general procedure using nonafluorobutyl iodide, C 4 F 9 I (9 equiv; 396 µl, 5.0x10-2 M) in 75% yield as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ): δ 7.03 (d, J = 9.0 Hz, 2H), 6.95 (d, J = 6.0 Hz, 1H), 3.82 (m, 3H), 3.79 (m, 3H); 19 F NMR (300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F), (t, J = 12.0 Hz, 2F),

11 (m, 2F), (m, 2F); HRMS (ESI, m/z): Cald. for C 12 H 10 F 9 O 2 [M+ H] ; found: ,4-Dimethoxy-2-(heptadecafluoro-n-octyl)benzene (3 C 8 F 17 ) C 8 F 17 3 C 8 F 17 Compound 3 C 8 F 17 was prepared according to the general procedure using heptadecafluoro-n-octyl iodide, C 8 F 17 I (9 equiv; 603 µl, 5.0x10-2 M) in 55% yield as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ): δ 7.04 (m, 2H), 6.95 (d, J = 9.0 Hz, 1H), 3.82 (m, 3H), 3.80 (m, 3H); 19 F NMR(300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F), (m, 2F), (m, 2F), (m, 6F), (m, 2F), (m, 2F); HRMS (ESI, m/z): Cald. for C 16 H 9 F 17 O 2 Na [M+Na] ; found: ,4-Dimethoxy-2-(heneicosafluorodecyl)benzene (3 C 10 F 21 ) C 10 F 21 3 C 10 F 21 Compound 3 C 10 F 21 was prepared according to the general procedure using heneicosafluorodecyl iodide, C 10 F 21 I (3 equiv; 492 mg, 5.0x10-2 M) in 10% yield as a white solid. 1 H NMR (300 MHz, CDCl 3 ): δ 7.04 (m, 2H), 6.98 (d, J = 9.0 Hz, 1H), 3.82 (m, 3H), 3.80 (m, 3H); 19 F NMR(300 MHz, CDCl 3 ): δ (t, J = 9.0 Hz, 3F), (brs, 2F), (brs, 2F), (m, 10F), (brs, 2F), (brs, 2F); HRMS (ESI, m/z): Cald. for C 18 H 9 F 21 O 2 Na [M+Na] ; found: ,2,4-Trimethoxy-5-(heptafluoropropyl)benzene (4 C 3 F 7 ) H 3 CO H 3 CO C 3 F 7 4 C 3 F 7 Compound 4 C 3 F 7 was prepared according to the general procedure using heptafluoropropyl iodide, C 3 F 7 I (9 equiv; 324 µl, 5.0x10-2 M) in 70% yield as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 6.94 (s, 1H), 6.58 (s, 1H), 3.94 (s, 3H), 3.86 (s, 3H),3.85 (s, 3H); 19 F NMR(400 MHz, CDCl 3 ): δ (t, J = 8.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 12 H 11 F 7 O 3 [M] ; found:

12 1,2,4-Trimethoxy-5-(nonafluorobutyl)benzene (4 C 4 F 9 ) H 3 CO H 3 CO C 4 F 9 4 C 4 F 9 Compound 4 C 4 F 9 was prepared according to the general procedure using nonafluorobutyl iodide, C 4 F 9 I (9 equiv; 387 µl, 5.0x10-2 M) in 69% yield as white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 6.94 (s, 1H), 6.58 (s, 1H), 3.94 (s, 3H), 3.86 (s, 3H), 3.85 (s, 3H); 19 F NMR(400 MHz, CDCl 3 ): δ (t, J = 8.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F); HRMS (EI, m/z):cald. for C 13 H 11 F 9 O 3 [M] ; found: ,2,4-Trimethoxy-5-(heptadecafluoro-n-octyl)benzene (4 C 8 F 17 ) H 3 CO H 3 CO C 8 F 17 4 C 8 F 17 Compound 4 C 8 F 17 was prepared according to the general procedure using heptafluoropropyl iodide, C 8 F 17 I (9 equiv; 594 µl, 5.0x10-2 M) in 48% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 6.95 (s, 1H), 6.59 (s, 1H), 3.94 (s, 3H), 3.87 (s, 3H),3.85 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0; 4.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 17 H 11 F 17 O 3 [M] ; found: ,2-Dimethoxy-4-(heptafluoropropyl)benzene (5 C 3 F 7 ) C 3 F 7 5 C 3 F 7 Compound 5 C 3 F 7 was prepared according to the general procedure using heptafluoropropyl iodide, C 3 F 7 I (9 equiv., 333 µl, 5.0x10-2 M) in 56% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 7.16 (dd, J = 12.0; 8.0 Hz, 1H), 7.02 (d, J= 4.0 Hz, 1H), 6.97 (d, J = 12.0 Hz, 1H), 3.94 (s, 3H), 3.92 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (t, J = 12.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 11 H 9 F 7 O 2 [M] ; found: ,2-Dimethoxy-4-(nonafluorobutyl)benzene (5 C 4 F 9 ) C 4 F 9 5 C 4 F 9 Compound 5 C 4 F 9 was prepared according to the general procedure using nonafluorobutyl iodide, C 4 F 9 I (9 equiv; 387 µl, 5.0x10-2 M) in 59% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 7.17 (dd, J = 12.0; 8.0 Hz, 1H), 7.03 (d, J= 4.0 Hz, 1H), 6.96 (d, J = 8.0 Hz, 1H), 3.94 (s, 3H), 12

13 3.92 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0; 8.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 12 H 9 F 9 O 2 [M] ; found: ,2-Dimethoxy-4-(heptadecafluoro-n-octyl)benzene (5 C 8 F 17 ) C 8 F 17 5 C 8 F 17 Compound 5 C 8 F 17 was prepared according to the general procedure using heptadecafluoro-n-octyl iodide, C 8 F 17 I (9 equiv; 593 µl, 5.0x10-2 M) in 47% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 7.17 (dd, J = 12.0; 8.0 Hz, 1H), 7.03 (d, J = 8.0 Hz, 1H), 6.97 (d, J = 8.0 Hz, 1H), 3.94 (s, 3H), 3.92 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0; 8.0 Hz, 3F), (t, J = 16 Hz, 2F), (m, 2F), (m, 6F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 16 H 9 F 17 O 2 [M] ; found: ,2-Dimethoxy-4-methyl-5-(heptafluoropropyl)benzene (6 C 3 F 7 ) H 3 CO H 3 CO 6 C 3 F 7 CH 3 C 3 F 7 Compound 6 C 3 F 7 was prepared according to the general procedure using Heptafluoropropyl iodide, C 3 F 7 I (9 equiv; 331 µl, 5.0x10-2 M) in 68% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 6.93 (s, 1H), 6.72 (s, 1H), 3.92 (s, 3H), 3.88 (s, 3H), 2.42 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (t, J = 12.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 12 H 11 F 7 O 2 [M] ; found: ,2-Dimethoxy-4-methyl-5-(nonafluorobutyl)benzene (6 C 4 F 9 ) Compound 6 C 4 F 9 was prepared according to the general procedure using H 3 CO CH 3 H 3 CO C 4 F 9 6 C 4 F 9 nonafluorobutyl iodide, C 4 F 9 I (9 equiv; 387 µl, 5.0x10-2 M) in 70% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 6.94 (s, 1H), 6.73 (s, 1H), 3.92 (s, 3H), 3.89 (s, 3H), 2.42 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0; 4.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 12 H 11 F 9 O 2 [M] ; found:

14 1,2-Dimethoxy-4-methyl-5-(heptadecafluoro-n-octyl)benzene (6 C 8 F 17 ) H 3 CO CH 3 H 3 CO C 8 F 17 6 C 8 F 17 Compound 6 C 8 F 17 was prepared according to the general procedure using heptadecafluoro-n-octyl iodide, C 8 F 17 I (9 equiv; 594 µl, 5.0x10-2 M) in 33% yield as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ): δ 6.94 (s, 1H), 6.72 (s, 1H), 3.92 (s, 3H), 3.89 (s, 3H), 2.42 (m, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (t, J = 8.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F), (m, 4F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 17 H 11 F 17 O 2 [M] ; found: ,3,5-Trimethyl-2-(heptafluoropropyl)benzene (7 C 3 F 7 ) C 3 F 7 7 C 3 F 7 Compound 7 C 3 F 7 was prepared according to the general procedure using heptafluoropropyl iodide, C 3 F 7 I (9 equiv; 324 µl, 5.0x10-2 M) in 38% yield as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ): δ 5.79 (s, 2H), 1.83 (s, 6H), 1.01 (s, 3H); 19 F NMR(300 MHz, CDCl 3 ): δ (t, J = 12.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 12 H 11 F 7 [M] ; found: Phenyl-2-(heptafluoropropyl)pyrrole (8 C 3 F 7 ) N C 3 F 7 8 C 3 F 7 Compound 8 C 3 F 7 was prepared according to the general procedure using heptafluoropropyl iodide, C 3 F 7 I (9 equiv; 324 µl, 5.0x10-2 M) in 55% yield as a colorless oil. 1 H NMR (400 MHz, C 6 D 6 ): δ (m, 2H), (m, 3H), (m, 1H), (m, 1H), (m, 1H); 19 F NMR (400 MHz, C 6 D 6 ): δ (tt, J = 12.0; 4.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 13 H 9 F 7 N [M] ; found: Phenyl-2-(nonafluorobutyl)pyrrole (8 C 4 F 9 ) N C 4 F 9 8 C 4 F 9 Compound 8 C 4 F 9 was prepared according to the general procedure using Nonafluorobutyl Iodide, C 4 F 9 I (9 equiv; 387 µl, 5.0x10-2 M) in 49% yield as a colorless oil. 1 H NMR (400 MHz, C 6 D 6 ): δ (m, 2H), (m, 3H), (m, 1H), (m, 1H), (m, 1H); 14

15 19 F NMR (400 MHz, C 6 D 6 ): δ (tt, J = 12.0; 4.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 14 H 9 F 9 N [M] ; found: Phenyl-2-(heptadecafluoro-n-octyl)pyrrole (8 C 8 F 17 ) N C 8 F 17 8 C 8 F 17 Compound 8 C 8 F 17 was prepared according to the general procedure using heptadecafluoro-n-octyl iodide, C 8 F 17 I (9 equiv; 594 µl, 5.0x10-2 M) in 37% yield as a colorless oil. 1 H NMR (400 MHz, C 6 D 6 ): δ (m, 2H), (m, 3H), (m, 1H), (m, 1H), (m, 1H); 19 F NMR (400 MHz, C 6 D 6 ): δ (tt, J = 12.0 Hz; 4.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F), (m, 4F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 18 H 9 F 17 N [M] ; found: ,2-dimethyl-3-(heptafluoropropyl)-1H-indole (9 C 3 F 7 ) C 3 F 7 N 9 C 3 F 7 Compound 9 C 3 F 7 was prepared according to the general procedure using Heptafluoropropyl Iodide, C 3 F 7 I (9 equiv; 324 µl, 5.0x10-2 M) in 61% yield as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 7.66 (d, J = 4.0 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), 3.72 (s, 3H), 2.51 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0 Hz; 4.0 Hz, 3F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 13 H 10 F 7 N [M] ; found: ,2-dimethyl-3-(nonafluorobutyl)-1H-indole (9 C 4 F 9 ) C 4 F 9 N 9 C 4 F 9 Compound 9 C 4 F 9 was prepared according to the general procedure using Nonafluorobutyl Iodide, C 4 F 9 I (9 equiv; 387 µl, 5.0x10-2 M) in 56% yield as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 7.66 (d, J = 4.0 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), 3.70 (s, 3H), 2.50 (s, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0; 4.0 Hz, 3F), (m, 2F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 14 H 10 F 9 N [M] ; found:

16 1,2-dimethyl-3-(heptadecafluoro-n-octyl)-1H-indole (9 C 8 F 17 ) C 8 F 17 N 9 C 8 F 17 Compound 9 C 8 F 17 was prepared according to the general procedure using heptadecafluoro-n-octyl iodide, C 8 F 17 I (9 equiv; 594 µl, 5.0x10-2 M) in 44% yield as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 7.67 (d, J = 8.0 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), 3.71 (s, 3H), 2.51 (S, 3H); 19 F NMR (400 MHz, CDCl 3 ): δ (tt, J = 12.0; 4.0 Hz, 3F), (m, 2F), ( )-( ) (m, 2F), ( )- ( ) (m, 6F), (m, 2F), (m, 2F); HRMS (EI, m/z): Cald. for C 18 H 10 F 17 N [M] ; found:

17 Table S1. Crystallographic Data of 2 CF 3 Sample 2 CF 3 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC C2/c (19) (2) (4) (3) (7)

18 Table S2. Crystallographic Data of 2 C 3 F 7 Sample 2 C 3 F 7 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC P (7) (7) (8) (10) (10) (10) (9)

19 Table S3. Crystallographic Data of 2 C 4 F 9 Sample 2 C 4 F 9 Size (mm) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC Pna (17) (6) (16) (6)

20 Table S4. Crystallographic Data of 2 C 8 F 17 Sample 2 C 8 F 17 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC C2/c 34.79(7) 5.967(12) 23.94(5) (5) (14)

21 Table S5. Crystallographic Data of 2 C 10 F 21 Sample 2 C 10 F 21 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC C2/c (3) (5) (2) (10) (7)

22 Table S6. Crystallographic Data of 4 C 3 F 7 Sample 4 C 3 F 7 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC P2 1 /c (11) 4.968(4) (13) (13) (17)

23 Table S7. Crystallographic Data of 9 C 4 F 9 Sample 9 C 4 F 9 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC P2 1 /n 7.024(3) 8.522(3) (9) (6) (9)

24 Table S8. Crystallographic Data of 9 C 8 F 17 Sample 9 C 8 F 17 Size (mm) Temperature (K) Space Group a (Å) b (Å) c (Å) α (º) β (º) γ (º) V (Å 3 ) Z Dcalc (g/cm 3 ) R 1 wr 2 GOF CCDC P (3) 9.755(4) (7) (7) (7) (7) 991.2(8)

25 1 H NMR CF 3 H 3 CO 2 CF 3 19 F NMR 25

26 1 H NMR C 3 F 7 H 3 CO 2 C 3 F 7 19 F NMR 26

27 1 H NMR C 4 F 9 H 3 CO 2 C 4 F 9 19 F NMR 27

28 1 H NMR C 8 F 17 H 3 CO 2 C 8 F F NMR 28

29 1 H NMR C 10 F 21 H 3 CO 2 C 10 F 21 29

30 C 10 F 21 H 3 CO 2 C 10 F F NMR 30

31 1 H NMR CF 3 3 CF 3 31

32 19 F NMR CF 3 3 CF 3 32

33 1 H NMR C 3 F 7 3 C 3 F 7 19 F NMR 33

34 1 H NMR C 4 F 9 3 C 4 F 9 34

35 C 4 F 9 19 F NMR 3 C 4 F 9 35

36 1 H NMR C 8 F 17 3 C 8 F 17 36

37 19 F NMR C 8 F 17 3 C 8 F 17 37

38 1 H NMR C 10 F 21 3 C 10 F 21 38

39 19 F NMR C 10 F 21 3 C 10 F 21 39

40 H 3 CO H 3 CO C 3 F 7 1 H NMR 4 C 3 F 7 19 F NMR 40

41 H 3 CO H 3 CO C 4 F 9 1 H NMR 4 C 4 F 9 41

42 H 3 CO H 3 CO C 4 F 9 19 F NMR 4 C 4 F 9 42

43 H 3 CO H 3 CO C 8 F 17 1 H NMR 4 C 8 F 17 43

44 H 3 CO 19 F NMR H 3 CO C 8 F 17 4 C 8 F 17 44

45 1 H NMR C 3 F 7 5 C 3 F 7 19 F NMR 45

46 1 H NMR C 4 F 9 5 C 4 F 9 19 F NMR 46

47 1 H NMR C 8 F 17 5 C 8 F F NMR 47

48 1 H NMR H 3 CO CH 3 H 3 CO C 3 F 7 6 C 3 F 7 48

49 19 F NMR H 3 CO CH 3 H 3 CO C 3 F 7 6 C 3 F 7 49

50 1 H NMR H 3 CO H 3 CO CH 3 C 4 F 9 6 C 4 F 9 19 F NMR 50

51 1 H NMR H 3 CO H 3 CO CH 3 C 8 F 17 6 C 8 F F NMR 51

52 1 H NMR C 3 F 7 7 C 3 F 7 19 F NMR 52

53 benzene 1 H NMR N C 3 F 7 (7.16) 8 C 3 F 7 water 19 F NMR 53

54 N C 4 F 9 benzene (7.16) 1 H NMR 8 C 4 F 9 water 19 F NMR 54

55 1 H NMR N C 8 F 17 benzene (7.16) 8 C 8 F 17 water 19 F NMR 55

56 1 H NMR C 3 F 7 N 9 C 3 F 7 19 F NMR 56

57 1 H NMR C 4 F 9 N 9 C 4 F 9 19 F NMR 57

58 1 H NMR C 8 F 17 N 9 C 8 F F NMR 58

59 Reference 1) Y. Murakami, Y. Hisaeda, A. Kajihara, Bull. Chem. Soc. Jpn. 1983, 56, ) F. Sladojevich, E. McNeill, J. Börgel, S.-L. Zheng, T. Ritter, Angew. Chem. Int. Ed. 2015, 54, ) Bruker AXS, SAINT, Bruker AXS Inc., Madison, WI, USA ) Bruker AXS, SADABS, Bruker AXS Inc., Madison, WI, USA ) Sheldrich, G. M. Acta Cryst. 2008, A64,

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