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1 Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in Water Yosuke Imanaka, 1 Hideki Hashimoto, 2,3 Isamu Kinoshita, 1,3 and Takanori Nishioka* 1 1 Department of Chemistry, Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka Department of Physics, Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka OCARINA, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka (Received January 10, 2014; CL ; nishioka@sci.osaka-cu.ac.jp) Copyright The Chemical Society of Japan

2 Supporting Information General Procedures: All chemicals were purchased from Aldrich, Nacalai Tesque and Wako Pure Chemical. All reagents and solvents were used without further purification. 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide (1), 1 1-(prop-2-ynyl)imidazole (2), 2 3-(2- bromoehtyl)-1-methylimidazolium bromide, 1 and PdCl 2 (NCCH 3 ) 4 2 were prepared according to the reported procedures. NMR spectra were recorded on JEOL Lambda (300 and 400 M Hz) and Bruker AVANCE (600 and 300 MHz) FT-NMR spectrometers. Electrospray ionization (ESI) mass spectrometry was performed on an Applied Biosystem Mariner time-of-flight mass spectrometer using HPLC grade solvents. Synthesis of 1-(2,3,4,6-tetra-O-acetyl-β-glucopyranosyl)-4-(1H-imidazol-1-ylmethyl)-1H-1,2,3- triazole 3: To a solution of 1-(prop-2-ynyl)imidazole (2) (0.96 g, 9.1 mmol) and 2,3,4,6-tetra-Oacetyl-β-glucopyranosyl azide (1) (1.99 g, 5.3 mmol) in 25 ml of DMF was added a solution of CuSO 4 5H 2 O (72 mg, 0.29 mmol) and sodium ascorbate (0.95 g, 4.8 mmol) in 5 ml of distilled water. The reaction mixture was stirred at room temperature overnight. The mixture was diluted S1

3 with 50 ml of water, and small amount of an aqueous solution of NH 3 (14%) was added to the solution. The mixture was extracted with ethyl acetate (50 ml 3). The separated organic layer was concentrated under reduced pressure, washed with an aqueous solution of NH 3 (14%, 20 ml 2) and brine, and dried over MgSO 4. The solvent was removed under reduced pressure to give the product as a light yellow solid (1.58 g, 62%) 1 H NMR (600 MHz, acetone-d6): δ 8.25 (1H, s, 5-Taz), 7.62 (1H, s, 2-Im), 7.09 (1H, s, 5-Im), 6.91 (1H, s, 4-Im), 6.23 (1H, d, 1-Glc, 3 J H-H = 8.9 Hz), 5.59 (1H, t, 2-Glc, 3 J H-H = 9.5 Hz), 5.53 (1H, t, 3-Glc, 3 J H-H = 9.5 Hz), 5.36 (1H, d, Taz-CH 2 -Im, 2 J H-H = 16.0 Hz), 5.33 (1H, d, Taz-CH 2 -Im), 5.25 (1H, t, 4-Glc, 3 J H-H = 9.6 Hz), 4.34 (1H, ddd, 5-Glc, 3 J H-H = 10.1 Hz, 3 J H-H = 5.3 Hz, 3 J H-H = 2.2 Hz), 4.24 (1H, dd, 6-Glc, 2 J H-H = 12.5 Hz, 3 J H-H = 5.3 Hz), 4.16 (1H, dd, 6-Glc, 2 J H-H = 12.6 Hz, 3 J H-H = 2.2 Hz), 2.02 (3H, s, 4-OAc), 1.97 (3H, s, 6-OAc), 1.96 (3H, s, 3-OAc), 1.77 (3H, s, 2-OAc). 13 C NMR (150 MHz, acetone-d 6 ): δ (C=O), (C=O), (C=O), (C=O), 145,0 (4-Taz), (2-Im), (4-Im), (5-Taz), (5-Im), (1-Glc), (5-Glc), (3-Glc), (2-Glc), (4-Glc), (6-Glc), (Taz-CH 2 -Im), (overlapped two OAc), (OAc), (OAc). Synthesis of ligand precursor 4: Compound 3 (1.01 g, 2.1 mmol) and 3-(2-bromoethyl)- 1-methylimidazolium bromide (0.56 g, 2.1 mmol) were dissolved in 20 ml of acetonitrile. After the mixture was heated at 111 C in a sealed tube for 6 days, the solvent was evaporated under reduced pressure. The obtained crude product was washed with acetone to give a gray solid, which was collected by filtration. (1.29 g, 81%) 1 H NMR (600 MHz, CD3CN): δ 9.69 (1H, s, 2-Im), 9.51 (1H, s, 2-Im), 8.52 (1H, s, 5-Taz), 7.88 (1H, s, 4-Im), 7.77 (1H, s, 5-Im), 7.54 (1H, s, 5-Im), 7.40 (1H, s, 4-Im), 6.25 (1H, d, 1-Glc, 3 J H-H = 9.3 Hz), 5.61 (2H, s, Taz-CH 2 -Im), 5.60 (1H, t, 2-Glc, 3 J H-H = 9.5 Hz), 5.49 (1H, t, 3-Glc, 3 J H-H = 9.6 Hz), 5.26 (1H, t, 4-Glc, 3 J H-H = 9.8 Hz), 4.94 (4H, s, Im-C 2 H 4 -Im), 4.28 (1H, ddd, 5-Glc, 3 J H-H = 10.1 Hz, 3 J H-H = 5.0 Hz, 3 J H-H = 2.3 Hz), 4.20 (1H, dd, S2

4 6-Glc, 2 J H-H = 12.6 Hz, 3 J H-H = 5.0 Hz), 4.14 (1H, dd, 6-Glc, 2 J H-H = 12.6 Hz, 3 J H-H = 2.2 Hz), 3.88 (3H, s, Im-CH 3 ), 2.00 (3H, s, OAc), 1.98 (3H, s, OAc), 1.95 (3H, s, OAc), 1.79 (3H, s, OAc). 13 C NMR (150 MHz, CD 3 CN): δ (C=O), (C=O), (C=O), (C=O), (4-Taz), (2-Im), (2-Im), (5-Taz), (4-Im), (4-Im), (5-Im), (5-Im), (1-Glc), 75.3 (5-Glc), (3-Glc), (2-Glc), (4-Glc), (6-Glc), (Im-CH 2 ), (Im-CH 2 ), (Im-CH 2 -Taz), (Im-CH 3 ), (OAc), (OAc), (OAc), (OAc). Synthesis of palladium complex 5: Ligand precursor 4 (500 mg, 0.67 mmol), [PdCl 2 (NCCH 3 ) 2 Cl 2 ] (174 mg, 0.67 mmol), and sodium acetate (128 mg, 1.6 mmol) were dissolved in 15 ml of DMSO. After the mixture was stirred at 60 C for 8 hours, the solvent of the mixture was removed under reduced pressure. The residue was dissolved in CH 3 CN, and insoluble solids were filtered off. Addition of diethyl ether into the filtrate gave a light yellow precipitate, which was collected by filtration. The solid was re-dissolved in methanol and the insoluble solid was removed by filtration. The solvent of the filtrate was evaporated to give a light yellow solid. The PF 6 salt was obtained by addition of a solution of KPF 6 in water into an aqueous solution of the light yellow solid, collected by filtration and washed with water. (325 mg, 57%) 1 H NMR (600 MHz, CD3CN): Major isomer: δ 8.25 (1H, s, 5-Taz), 7.30 (1H, s, 4,5-Im), 7.28 (1H, d, 4,5-Im, 3 J H-H = 1.9 Hz), 7.17 (1H, d, 4,5-Im, 3 J H-H = 1.8 Hz), 7.05 (1H, d, 4,5-Im, 3 J H-H = 1.9 Hz), 6.10 (1H, d, 1-Glc, 3 J H-H = 9.2 Hz), (1H, m, Im-C 2 H 4 -Im), 5.53 (1H, t, 3-Glc, 9.5 Hz), (2H, m, Taz-CH 2 -Im), 5.43 (1H, t, 2-Glc, 3 J H-H = 9.7 Hz), 5.28 (1H, t, 4-Glc, 3 J H-H = 9.5 Hz), (1H, m, Im-C 2 H 4 ), (1H, m, Im-C 2 H 4 ), (1H, m, Im-C 2 H 4 ), (3H, m, 5,6-Glc), 3.90 (3H, s, Im-CH 3 ), 2.03 (3H, s, OAc), 2.00 (3H, s, OAc), 1.99 (3H, s, OAc), 1.97 (3H, s, OAc). Minor isomer: δ 8.28 (1H, s, 5-Taz), 7.30 (2H, s, 4,5-Im), 7.17 (1H, d, 4,5-Im, 3 J H-H = 1.8 Hz), 7.17 (1H, S3

5 d, 4,5-Im, 3 J H-H = 1.8 Hz), 7.07 (1H, d, 4,5-Im, 3 J H-H = 1.8 Hz), 6.12 (1H, d, 1-Glc, 3 J H-H = 9.3 Hz), (1H, m, Im-C 2 H 4 -Im), 5.58 (1H, t, 2-Glc, 9.4 Hz), 5.49 (1H, t, 3-Glc, 9.5 Hz), (2H, s, Taz-CH 2 -Im), 5.28 (1H, t, 4-Glc, 3 J H-H = 9.7 Hz), (1H, m, Im-C 2 H 4 ), (1H, m, Im-C 2 H 4 ), (1H, m, Im-C 2 H 4 ), (3H, m, 5,6-Glc), 3.90 (3H, s, Im-CH 3 ), 2.02 (3H, s, OAc), 2.01 (3H, s, OAc), 1.97 (3H, s, OAc), 1.85 (3H, s, OAc). 13 C NMR (150 MHz, CD 3 CN): Major isomer: δ (C=O), (C=O), (C=O), (C=O), (2-Im), (2-Im), (4-Taz), (4,5-Im), (4,5-Im), (4,5-Im), (5-Taz), (4,5-Im), (1-Glc), (5-Glc), (3-Glc), (2-Glc), (4-Glc), (6-Glc), (Im-C 2 H 4 -Im), (Im-C 2 H 4 -Im), (Taz-CH 2 -Im), (Im-CH 3 ), (OAc). Minor isomer: δ (C=O), (C=O), (C=O), (C=O), (2-Im), (2-Im), (4-Taz), (4,5-Im), (4,5-Im), (4,5-Im), (5-Taz), (4,5-Im), (1-Glc), (5-Glc), (3-Glc), (2-Glc), (4-Glc), (6-Glc), (Im-C 2 H 4 -Im), (Im-C 2 H 4 -Im), (Taz-CH 2 -Im), (Im-CH 3 ), (OAc). ESI-MS: m/z = 730 ([M PF 6 ] + ). Anal. Calcd for C 26 H 33 ClF 6 N 7 O 9 PPd 2H 2 O: C, 34.30; H, 4.10; N, 10.77, Found: C, 34.21; H, 3.89; N, 10.73% (The integrated intensity of the signal of H 2 O in 1 H NMR spectrum of the complex in dry CDCl 3 was 3.19 (1.6 equiv. of H 2 O) relative to the sum of the integrated intensity of the 5-H of the triazole in the complex.) Line shape analyses of VT-NMR spectra of 5 in DMSO-d 6 : Line shape analyses were performed for the signals of the 5-triazole proton in 5 at variable temperature using Chemical Exchange program in NMR v4 software package. Obtained kinetic constants were used to obtain the activation parameters; ΔH = 49.3(4) kj mol 1, ΔS = 74(1) J mol 1 K 1 and ΔG 298K = 71.3(7) kj mol 1. S4

6 Fig. S1 Variable temperature 1H NMR spectra of 5 at 25, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130,140 and 150 ºC from bottom to top. Fig. S2 Observed (left) and simulated (right) signals of the 5-triazole proton in VT-NMR spectra of 5 in DMSO-d6 S5

7 Fig. S3 Eyring plot for line shape analyses of 5 Representative procedure for Suzuki-Miyaura cross-coupling reactions in water: Complex 5 as a catalyst (1 mol%), 4'-bromoacetophenone (0.2 mmol), phenylboronic acid (0.3 mmol), K 2 CO 3 (0.4 mmol) and 1.0 ml of water were charged into a sealed tube. The sealed tube was placed in a preheated oil bath (100 C) for 16 h. The reaction mixture was extracted with dichloromethane three times. The combined organic phase was dried with anhydrous MgSO 4 and the solvent was evaporated under reduced pressure. The yield of the product was determined by integral intensities of the 1 H NMR signals of the products and the starting materials using 1,3,5-trimethoxybenzene as an internal standard. Reactions of 4'-bromoacetophenone using phenylboronic acid in water using 5 as a catalyst Table S1 Results of Suzuki-Miyaura cross-coupling reaction of 4 -bromoacetophenone and phenylboronic acid catalyzed by 5 in water Entry Cat/mol% Std/mmol Ratio of Int Yield/mmol Yield/% TON , , ,000 S6

8 Fig. S4 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction of 4 -bromoacetophenone and phenylboronic acid with 1 mol% of 5 as a catalyst. (Entry 1) Fig. S5 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction of 4 -bromoacetophenone and phenylboronic acid with 0.01 mol% of 5 as a catalyst. (Entry 2) Fig. S6 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction of 4 -bromoacetophenone and phenylboronic acid with mol% of 5 as a catalyst. (Entry 3) S7

9 Fig. S7 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction of 4 -bromoacetophenone and phenylboronic acid with mol% of 5 as a catalyst. (Entry 4) Reactions of 4'-chloroacetophenone using phenylboronic acid in water using 5 as a catalyst Table S2 Results of Suzuki-Miyaura cross-coupling reaction of 4 -bromoacetophenone and phenylboronic acid catalyzed by 5 in water Entry Time/h Cat/mol% Std/mmol Ratio of Int Yield/mmol Yield/% TON Fig. S8 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction for 17h of 4 -chloroacetophenone and phenylboronic acid with 0.5 mol% of 5 as a catalyst. (Entry 5) S8

10 Fig. S9 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction for 17h of 4 -chloroacetophenone and phenylboronic acid with 0.5 mol% of 5 as a catalyst. (Entry 6) Fig. S10 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction for 17h of 4 -chloroacetophenone and phenylboronic acid with 0.5 mol% of 5 as a catalyst. (Entry 7) Fig. S11 1 H NMR spectrum in CDCl 3 obtained from the catalytic reaction for 41h of 4 -chloroacetophenone and phenylboronic acid with 0.5 mol% of 5 as a catalyst. (Entry 8) S9

11 Fig. S12 1H NMR spectrum in CDCl3 obtained from the catalytic reaction for 41h of 4 -chloroacetophenone and phenylboronic acid with 0.5 mol% of 5 as a catalyst. (Entry 9) Deprotection of 5 in D2O using sodium carbonate: Deprotection reaction in water in the presence of s K2CO3 was examined using 1H NMR spectroscopy and ESI-MS. A mixture of 5 and K2CO3 in D2O was heated at 100 ºC for 1 hour in a NMR tube. 1H NMR spectrum of the resulting solution and ESI-mass spectrum of a sample, which was made by dilution of the solution with MeOH, were shown in Figs. S13 and S14. Although the signal of the 5-H of the triazole moiety was not observed because deuteration occurred at the position under the basic condition in D2O due to the higher acidity of the proton, the 1H NMR spectrum revealed the signals for the deprotected ligand showing the deprotection reaction successfully proceeded. The mass spectrum, which exhibited signals at [M PF6+1]+, also supports the deuteration. Fig. S13 1H NMR spectrum of in-situ generated deprotected 5 in D2O. S10

12 Fig. S14 ESI- mass spectrum of diluted sample in MeOH of in-situ generated deprotected 5 in D 2 O. References 1 T. Ogawa, S. Nakabayashi, S. Shibata, Agric. Biol. Chem. 1983, 47, L. I. Vereshchagin, A. V. Petrov, A. G. Proidakov, F. A. Pokatilov, A. I. Smirnov, V. N. Kizhnyaev, Russ. J. Org. Chem. 2006, 42, L. D. Field, B. A. Messerle, K. Q. Vuong, P. Turner, Organometallics 2005, 24, M. Rimoldi, F. Ragaini, E. Gallo, F. Ferretti, P. Macchi, N. Casati, Dalton Trans. 2012, 41, S11

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