Derivatives. Republic. Supporting Information. Index. General Considerations. Experimental Procedures and Spectroscopic Data

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1 Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives Jan Storch *, Jan Sýkora, Jan Čermák, Jindřich Karban, Ivana Císařová and Aleš Růžička Institute of Chemical Process Fundamentals, AS CR, Rozvojova 135, CZ Prague 6, Czech Republic Supporting Information Index General Considerations Experimental Procedures and Spectroscopic Data X-ray diffraction data for 7a, 7b and 8b Spectra References S2 S3 S5 S10 S21 S1

2 General Considerations. Electron impact (EI) mass spectra were determined at an ionising voltage of 70 ev. 1 H and 13 C{1H} spectra were measured at and MHz, respectively and at and MHz, respectively. Chemical shifts are reported in ppm (d) relative to TMS, referenced to signal CDCl 3 or C 2 D 2 Cl 4. HPLC-NMR apparatus: A commercial HPLC system mm C 18 (5 µm particles, 300 Ǻ pore size), was employed in the LC-NMR experiment. 50 µl of the acetonitrile solution (approx. concentration 50 mg/ml) was injected into the system using gradient elution of acetonitrile and D 2 O mixture (starting conditions acetonitrile/d 2 O=50:50 going to pure acetonitrile in 30 min, followed by 10 mins of isocratic acetonitrile) with the flow rate 0.5 ml/min with UV detection at 310 nm. 1 H NMR observations were conducted on 500 MHz spectrometer equipped with HCN triple resonance (60 µl active volume) microflow probe. All the separations and NMR detection were conducted at ambient temperature (22 o C). Data were collected in on-flow mode employing WET multiple frequency solvent suppression 1 to suppress signals from acetonitrile and HOD using a scout scan at the start of each incerement consisting of four transients. The data accumulation during 1 s acquisition time covering the spectral width 10 khz followed after 90 RF pulse (3.4 µs). Data were zero-filled to 32K and the initial 3 data points were obtained by backward projection (32 LP coefficients) and the residual signals of water and acetonitrile were eliminated by digital solvent subtraction before Fourier transform. The 1 H NMR signal of acetonitrile served as a chemical shift reference (2.00 ppm). Commercially available reagent grade materials were used as received. THF was freshly distilled from sodium/benzophenone under an atmosphere of nitrogen. TLC was performed on Silica gel 60 F254- coated aluminium sheets and compounds were visualized by UV light (254 nm). Crystallographic data: The diffraction-quality crystals of complexes were grown as mentioned in the article. The crystals were selected in mother liquor and quickly transferred into an oil, then mounted on glass fibres in random S2

3 orientation and cooled to 150(1) K. Diffraction data were collected using CCD diffractometer at 150(1) K. The structures were solved by direct methods and refined by full-matrix least-squares techniques on F values. The crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication. Copies of the data can be obtained free of charge on application to CCDC, deposit@ccdc.cam.ac.uk. Experimental Procedures and Spectroscopic Data 2-bromo-3-iodophenol (1b): To a solution of methyl ether 1c (10 g, 32 mmol) in dichloromethane (150 ml) was added BBr 3 (24.05 g, 96 mmol, 3 equiv) dropwise. The mixture was stirred at r.t. for 3 h. The mixture was diluted with water (100 ml), extracted with dichloromethane (3 x 80 ml), the combined organic portions were dried with anhydrous MgSO 4 and the solvent was evaporated in vacuo. The residue was filtered through a pad of silica gel (hexane/ethyl acetate, 3:1) to afford phenol 1b (9.0 g, 94%) as a yellow orange oil that solidified upon standing: mp C. The product was spectrally identical to previously reported sample. 2 General Procedure for the Synthesis of Propynyl Derivatives 2: Propyne was bubbled for 1-2 hour into a mixture of iodide 1a, 1b or 1c (20 mmol), triethylamine (200 ml), [PdCl 2 (PPh 3 ) 2 ] (0.7 g, 1 mmol, 0.05 equiv), and CuI (0.38 g, 2 mmol, 0.1 equiv), leading to the discoloration of the solution and the formation of a brownish precipitate. Bubbling was discontinued at that stage and the resulting mixture was stirred under the remaining propyne atmosphere for 20 h at ambient temperature during which it turned black. For work-up, the reaction mixture was diluted with saturated solution of NH 4 Cl (200 ml), extracted with dichloromethane (3 x 100 ml), the combined organic portions were dried with anhydrous S3

4 MgSO 4 and the solvents were evaporated in vacuo. The black residue was dissolved and filtered twice through a pad of silica gel (hexane/ethyl acetate, 3:1) to afford propynyl derivatives 2a c. 1-bromo-2-(propyn-1-yl)benzene (2a): 1a (5.7 g, 20 mmol) was used according to general procedure. Yield 3.7 g (94%) of slightly yellow oil. The product was spectrally identical to previously reported sample. 3 2-bromo-3-(propyn-1-yl)phenol (2b): 1b (6.0 g, 20 mmol) was used according to general procedure. Yield 3.9 g (93%) of slightly yellow oil. 1 H NMR (300 MHz; CDCl 3 ): δ 7.12 (t, J = 7.9 Hz, 1H), 7.01 (dd, J = 1.5, 7.6 Hz, 1H), 6.94 (dd, J = 1.5, 8.0 Hz, 1H), 2.34 (s, 3H). 13 C NMR (75 MHz; CDCl 3 ): δ (s), (d), (s), (d), (d), (s), 91.0 (s), 78.2 (s), 4.6 (q). MS (EI): m/z 210 (100% M + ), 131, 103, 77, 63, 51. Anal. Calcd for C 9 H 7 BrO: C, 51.22; H, Found: C, 51.09; H, General Procedure for the Synthesis of Boronic acid 3: To a solution of 2a or 2c (51.3 mmol) in 80 ml of THF was slowly added 22.6 ml of n-butyllithium (2.5 M in hexanes, 56.4 mmol, 1.1 equiv) at - 78 C. The mixture was stirred for 3 min and 16.0 g (17.2 ml, 0.15 mol, 3 equiv) of trimethylborate was added. The reaction mixture was stirred at this temperature for 30 min then warmed up to ambient temperature overnight. To the reaction mixture was added 100 ml of 2N HCl and this solution was stirred for 1 hour. Then it was diluted with 100 ml of diethyl ether and the layers were separated. While the aqueous layer was stirred, its ph was adjusted to 7 using a 5 N NaOH solution. A white solid product precipitated as the ph approached 7. Mixture was extracted three times with diethyl ether (50 ml), combined etheral extracts were dried and evaporated in vacuo to provide a solid product. 2-(propyn-1-yl)phenylboronic acid (3a): 2a (10 g, 51.3 mmol) was used according to general procedure. Yield 3.45 g (42%) of slightly yellow solid. 1 H NMR (300 MHz; CDCl 3 ): δ (m, 1H), (m, 3H), 6.49 (s, 2H), 2.13 (s, 3H). 13 C NMR (75 MHz; CDCl 3 ): δ (d), (d), S4

5 130.9 (d), (d), (s), 90.7 (s), 81.1 (s), 4.6 (q), C(1) not observed. MS (EI): m/z 115 (100%, M + - BOOH), 89, 63, 58, 51, 39. Anal. Calcd for C 9 H 9 BO 2 : C, 67.57; H, Found: C, 67.44; H, General Procedure for the Synthesis of Biphenylyl-naphthalenes 6 and 7: A mixture of Pd(PPh 3 ) 4 (200 mg, 0.17 mmol, 10 mol%) and triflate 5 (0.7 g, 1.8 mmol) in toluene (9 ml) was stirred for 5 min at room temperature under argon. 2 M aqueous Na 2 CO 3 (4.5 ml, 9 mmol, 5 equiv) was added to the mixture, followed by the corresponding boronic acid 3a or 3b in ethanol (9 ml). The mixture was heated at 73 C for 20 h, then cooled to room temperature, diluted with water and extracted with diethyl ether. Organic phase was filtered through a pad of flash silica gel, eluting with hexane:ethyl acetate (3:1).The solvents were removed in vacuo, and the residue was purified by column chromatography. 1-(2',3-di(propyn-1-yl)biphenyl-2-yl)naphthalene (6): 3a (0.4 g, 2.5 mmol, 1.4 equiv) was used according to general procedure. Purification by column chromatography on silica gel 60 RP-C18 (acetonitrile:water, 80:20 to 100:0) gave 6 (0.29 g, 45%) as a colorless oil. 1 H NMR at 75 C (500 MHz; C 2 D 2 Cl 4 ): δ 7.76 (dd, J = 0.9, 8.3 Hz, 1H), (m, 2H), 7.60 (dd, J = 1.5, 7.6 Hz, 1H), 7.48 (dd, J = 1.5, 7.8 Hz, 1H), 7.43 (t, J = 7.6 Hz, 1H), (m, 4H), 7.24 (d, J = 7.6 Hz, 1H), 6.93 (dt, J = 1.6, 7.6 Hz, 1H), 6.81 (t, J = 8.0 Hz, 1H), 6.78 (d, J = 7.2 Hz, 1H), 1.95 (s, 3H), 1.54 (s, 3H). 13 C NMR at 75 C ( MHz; C 2 D 2 Cl 4 ): δ (s), (s), (s), (s), (s), (d), (d), (d), (d), (d), (d), (s), (d), (d), (d), (d), (d), (s), (d, 2C), (d), (s), 89.4 (s), 89.0 (s), 79.4 (s, 2C), 4.2 (q), 3.7 (q). MS (EI): m/z 356 (60% M + ), 341, 326, 313, 163. Anal. Calcd for C 28 H 20 : C, 94.34; H, Found: C, 94.14; H, General Procedure for the Cycloizomerization to Hexahelicenes 8: A solution of 6 or 7 (1.3 mmol) and PtCl 2 (34.6 mg, 0.13 mmol, 10 mol%) in toluene (10 ml) was stirred for 20 h at 90 C. The solvent was evaporated and the residue was purified by column chromatography. S5

6 6,10-dimethylhexahelicene (8a): 6 (0.46 g, 1.3 mmol) was used according to general procedure. Purification by column chromatography on silica gel 60 RP-C18 (acetonitrile) gave 0.37 g (80%) of 8a as a colorless oil. 1 H NMR (500 MHz; CDCl 3 ): δ 8.16 (d, J = 8.4 Hz, 1H), 8.14 (d, J = 8.8 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.8 Hz, 1H), 7.84 (s, 1H), 7.81 (d, J = 7.9 Hz, 1H), 7.73 (s, 1H), 7.70 (d, J = 7.9 Hz, 1H), 7.57 (d, J = 8.5 Hz, 1H), 7.44 (d, J = 8.5 Hz, 1H), 7.19 (t, J = 7.4 Hz, 1H), 7.14 (t, J = 7.4 Hz, 1H), 6.66 (t, J = 7.7 Hz, 1H), 6.57 (t, J = 7.6 Hz, 1H), 2.92 (s, 6H). 13 C NMR ( MHz; CDCl 3 ): δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (d), (d), (d), (d), (d), (d), (d), (d), (d), (d), (d), (d), (d), (d), 20.4 (q), 19.9 (q). MS (EI): 356 (100% M + ), 340, 326, 314, 178, 170, 163, 156, 143. Anal. Calcd for C 28 H 20 : C, 94.34; H, Found: C, 94.40; H, X-ray data for 7a: C 29 H 22 O, M= g/mol, triclinic system, space group P -1, a= (3), b= (3), c= (7) Å, α= (2), β= (2), γ= (2), V= (7)Å 3, Z=2, D c = 1.21 g.cm -3, µ(mo Kα)= 0.07 mm -1, crystal dimensions of 0.2 x 0.2 x 0.3 mm. The structure was refined anisotropically to final R=0.039 and R w =0.042 using 3761 independent reflections (θ max =27.13, 359 parameters). Hydrogen atoms were located from expected geometry and were refined isotropically. Crystallographic data were deposited in CSD under CCDC registration number X-ray data for 7b: C 29 H 22 O, M= g/mol, triclinic system, space group P -1, a= (3), b= (3), c= (3) Å, α= (1), β= (1), γ= (2), V= (5)Å 3, Z=2, D c = 1.21 g.cm -3, µ(mo Kα)= 0.07 mm -1, crystal dimensions of 0.1 x 0.1 x 0.2 mm. The structure was refined anisotropically to final R=0.040 and R w =0.045 using 3761 independent reflections (θ max =27.47, 359 parameters). Hydrogen atoms were located from expected geometry and were refined isotropically. Crystallographic data were deposited in CSD under CCDC registration number S6

7 X-ray data for 8: C 29 H 22 O, M= g/mol, monoclinic system, space group P 21/c, a= (4), b= (2), c= (2) Å, β= (6), V= (4)Å 3, Z=2, D c = 1.28 g.cm -3, µ(mo Kα)= 0.07 mm -1, crystal dimensions of 0.05 x 0.2 x 1 mm. The structure was refined anisotropically to final R=0.071 and R w =0.061 using 2300 independent reflections (θ max =27.50, 359 parameters). Hydrogen atoms were located from expected geometry and were refined isotropically. Absorption correction using Gaussian integration from crystal shape was carried on. Crystallographic data were deposited in CSD under CCDC registration number S7

8 Figure S8. Pseudo 2D NMR spectrum showing the separation of the product 7 from reaction mixture. 7a and 7b elute at 27 and 29 minute, respectively. S8

9 Figure S9. ORTEP projection of the crystal structure of hexahelicene 8b, P type. S9

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15 S15

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17 S17

18 S18

19 S19

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21 REFERENCES. (1) Smallcombe, S. H.; Patt, S.L.; Keifer, P.A. J. Magn. Reson. 1995, 117, 295. (2) Sanz, R.; Castroviejo, M. P.; Fernández, Y.; Fañanás, F. J. J. Org. Chem. 2005, 70, (3) Sashida, H.; Sadamori, K.; Tsuchiya, T. Synth. Commun. 1998, 28, 713. S21

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