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1 Supporting Information for Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis Koji Endo and Robert H. Grubbs* Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States Contents 0. General Information S2 1. Experimental details on syntheses S Synthesis of 1b S Synthesis of silver pivalate (S2) S Synthesis of 4a S Observation of 3a S Synthesis of 4b S3 2. Experimental details on metathesis assays S Representative procedure for RCM of S Representative procedure for ROMP of S Representative procedure for CM of 9 and S CM of 9 and 10 in a synthetic scale S4 3. References S4 List of Figures and Tables Figure S1. X-ray crystal structure and selected bond length of 1b S4 Figure S2. 1 H NMR spectrum of 1b S5 Figure S3. 13 C NMR spectrum of 1b S5 Figure S4. 1 H NMR spectrum of 4a S6 Figure S5. 13 C NMR spectrum of 4a S6 Figure S6. 1 H NMR spectrum of a reaction mixture containing 3a and 4a S7 Figure S7. 1 H NMR spectrum of 4b S7 Figure S8. 13 C NMR spectrum of 4b S8 Figure S9. GC spectrum of a mixture of Z-11 and E S9 Figure S10. GC spectrum of a mixture of Z-12 and E S10 Table S1. Data for RCM of 5 by 4a S11 Table S2. Data for RCM of 5 by 4b S12 Table S3. Data for ROMP of S13 Table S4. GC response factors and retention times S13 Table S5. Data for CM of 9 and 10 by 4a S13 Table S6. Data for CM of 9 and 10 by 4b S14 Table S7. Data for CM of 9 and 10 by 1a S14 Table S8. Data for CM of 9 and 10 by 1b S14 S1

2 0. General Information Atmosphere All reactions were carried out in dry glassware under an argon atmosphere using standard Schlenk techniques or in a Vacuum Atmospheres Glovebox under a nitrogen atmosphere unless otherwise specified. Solvents Hexane was dried over CaH 2 and vacuum transferred to a dry Schlenk flask and subsequently degassed with argon. Et 2 O and CH 2 Cl 2 for 1-1, H 2 O, MeOH and hexane for 1-2, isopropyl alcohol and CH 2 Cl 2 for and hexane and ethyl acetate for 2-4 were used as received. THF-d 8 and DMSO-d 6 were used as received. All the other solvents were purified by passage through solvent purification columns and further degassed with argon. S1 Materials 1-(1-Adamantyl)-3-(2,4,6-trimethylphenyl)imidazolinium chloride (2) was purchased from Aldrich and used without purification. Potassium t-amyloxide was purchased as toluene solution and dried before use. Dichloro(o-isopropoxyphenylmethylene)(tricyclehexylphosphine)ruthenium (S1) and 1a were obtained from Materia, Inc. 5 was purified by distillation over CaH 2. 7 was purified by sublimation. Tridecane, 9 and 10 were distilled over CaH 2 and stored under nitrogen in Schlenk flasks. Other commercially available reagents and silica gel were used as received. Instruments 1 H and 13 C NMR spectra were recorded on a Varian 500 Mhz spectrometer or a Varian 300 Mhz spectrometer. Highresolution mass spectra were provided by the California Institute of Technology Mass Spectrometry Facility using JEOL JMS-600H High Resolution Mass Spectrometer. X-ray crystallographic data were collected by the California Institute of Technology Beckman Institute X- ray Crystallography Facility using Bruker KAPPA APEXII X-ray diffractometer. Gas chromatography data were obtained using Agilent 6850 FID gas chromatograph equipped with a DB-Wax polyethylene glycol capillary column (Agilent). 1. Experimental details on syntheses 1-1. Synthesis of 1b S2 2 (496 mg, 1.38 mmol), potassium t-amyloxide (175 mg, 1.38 mmol) and hexane (30 ml) were placed in a 50 ml 2-necked flask equipped with a 3-way stopcock and a magnetic stir bar. After stirring at room temperature for 1 h, S1 (800mg, 1.33 mmol) was added. While the dark red-brown solution was stirred at 60 o C for 4 h, green solid was precipitated. After cooling to room temperature, the green solid was collected on a filter and washed with Et 2 O (20 ml x 3 times). The resulting solid was extracted with CH 2 Cl 2 (30 ml) and then volatiles were evaporated. After dry under high vacuum, 1b was obtained as air-stable bright green solid (785 mg, 1.22 mmol, 91.7% yield based on S1). A crystal for X-ray crystallography was made by recrystallization in which pentane was added onto concentrated solution of 1b in CH 2 Cl 2. X-ray crystal structure and selected bond length of 1b are shown in Figure S1. 1 H NMR (500 MHz, C 6 D 6 ): δ/ppm (s, 1H), (m, 2H), 6.85 (s, 2H), (m, 1H), 6.46 (d, J = 8.2 Hz, 1H), 4.58 (sep, J = 6.1 Hz, 1H), (m, 4H), 2.95 (br s, 6H), 2.35 (s, 6H), 2.31 (br s, 3H), 2.24 (s, 3H), 1.90 (br d, 3H), 1.69 (br d, 3H), 1.58 (d, J = 6.1 Hz, 6H). 13 C NMR (125.7 MHz, C 6 D 6 ): δ/ppm 307.9, 210.4, 153.1, 146.8, 140.7, 138.8, 138.6, 130.3, 130.2, 123.7, 122.8, 113.9, 74.6, 57.5, 51.4, 44.7, 42.6, 36.7, 30.8, 22.8, 21.5, HRMS (FAB+): Calculated: , Found: Synthesis of silver pivalate (S2) S3 All procedures except vacuum dry were carried out under air. Pivalic acid (2.13 g, 20.9 mmol) was added to a solution of NaOH (723 mg, 18.1 mmol) in H 2 O (10 ml) in a 50 ml beaker equipped with a magnetic stir bar. After stirring at room temperature for 15 min, a solution of AgNO 3 (2.56 g, 15.1 mmol) in H 2 O (10 ml) was added dropwise. During the addition, white precipitate appeared. After stirring the white slurry at room temperature for 15 min, the white solid was collected on a filter and then washed by H 2 O (20 ml x 3 times), MeOH (20 ml x 3 times) and hexane (20 ml x 3 times), respectively. Subsequent drying under vacuum afforded S2 as white solid (2.62 g, 12.5 mmol, 83.2% yield based on AgNO 3 ). S2 was kept under dark for stock. 1 H NMR (300 MHz, DMSO-d 6 ): δ/ppm 1.12 (s, 9H). S2

3 1-3. Synthesis of 4a In a glove box, 1a (300 mg, 479 µmol), S2 (210 mg, 1.01 mmol) and THF (10 ml) were added into a 20 ml vial equipped with a magnetic stir bar. The reaction mixture was stirred at room temperature under dark for 2 h and then filtered. The filtrate was evaporated and the resulting solid was washed with a mixture of pentane and Et 2 O (4:1, 10 ml x 3 times). After dry under high vacuum, 4a was obtained as air-stable dark green solid (129 mg, 197 µmol, 41.2% yield based on 1a). A crystal for X-ray crystallography was made by recrystallization from concentrated solution of 4a in Et 2 O at -20 o C. 1 H NMR (500 MHz, C 6 D 6 ): δ/ppm (s, 1H), (m, 2H), 7.06 (s, 1H), 6.95 (s, 1H), 6.92 (s, 1H), (m, 1H), 6.63 (s, 1H), 6.49 (d, J = 8.5 Hz, 1H), 4.68 (sep, J = 6.4 Hz, 1H), (m, 1H), (m, 2H), 3.29 (d, J = 9.8 Hz, 1H), (m, 1H), 2.46 (s, 3H), 2.36 (s, 3H), 2.26 (s, 3H), 2.21 (s, 3H), 2.17 (d, J = 9.8 Hz, 1H), 2.12 (s, 3H), 1.48 (d, J = 6.4 Hz, 3H), 1.26 (s, 9H), 1.16 (d, J = 6.4 Hz, 3H). 13 C NMR (125.7 MHz, C 6 D 6 ): δ/ppm 280.8, 223.6, 186.6, 154.6, 144.7, 142.7, 142.3, 139.7, 138.4, 137.7, 136.8, 134.5, 130.9, 130.7, 128.8, 128.1, 128.0, 126.9, 123.6, 123.1, 112.7, 54.1, 50.3, 39.5, 28.5, 22.2, 21.7, 21.4, 21.3, 19.9, 18.7, 18.6, HRMS (FAB+): Calculated: , Found: Observation of 3a In a glove box, 1a (5.0 mg, 8.0 µmol), S2 (3.3 mg, 16 µmol) and THF-d 8 (800 µl) were added into an NMR tube equipped with a screw-cap. The reaction mixture was allowed to stand at room temperature under dark with shaken several times. After 30 min, 1 H NMR was measured and signals of alkylidene protons were observed at δ = ppm (br s, 3a) and ppm (s, 4a). Then small portion of the reaction mixture was collected and analyzed by FAB-MS. The MS spectrum showed signals assigned to 3a (M/z = 757 (M-H)) and 4a (M/z = 656 (M)), respectively. The reaction mixture was allowed to stand further 1.5 h. and then 1 H NMR was measured. In the 1 H NMR spectrum, only 4a was detected as an alkylidene complex in the spectrum Synthesis of 4b In a glove box, 1b (2.19 g, 3.41 mmol), S2 (2.23 g, 10.7 mmol) and THF (50 ml) were added into a 100 ml flask equipped with a magnetic stir bar. The reaction mixture was stirred at room temperature under dark for 10 min and then filtered. The filtrate was evaporated and the resulting solid was washed with a mixture of pentane and Et 2 O (4:1, 20 ml x 3 times). Resulting crude solid was extracted with C 6 H 6 and evaporated. After dry under high vacuum, 4b was obtained as air-stable purple solid (1.36 g, 2.02 mmol, 59.3% yield based on 1b). A crystal for X-ray crystallography was made by recrystallization from concentrated solution of 4b in THF at -20 o C. 1 H NMR (500 MHz, C 6 D 6 ): δ/ppm (s, 1H), 7.47 (dd, J = 7.3 Hz, J = 1.2 Hz, 1H), (m, 1H), 6.90 (t, J = 7.3 Hz, 1H), 6.82 (s, 1H), 6,74 (s, 1H), 6.71 (d, J = 8.2 Hz, 1H), 4.80 (sep, J = 6.4 Hz, 1H), 4.19 (s, 1H), (m, 2H), (m, 2H), 2.53 (br s, 1H), 2.43 (s, 3H), 2.27 (s, 3H), 2.20 (s, 3H), (br m, 2H), (br m, 1H), (br m, 1H), (br m, 1H), (br m, 1H), (br m, 2H), 1.52 (d, J = 6.4 Hz, 3H), (br m, 1H), 1.25 (s, 9H), (br m, 1H), 1.17 (d, J = 6.4 Hz, 3H), (br m, 1H), (br m, 1H). 13 C NMR (125.7 MHz, C 6 D 6 ): δ/ppm 258.9, 216.0, 154.6, 144.2, 138.3, 137.4, 137.1, 136.7, 130.2, 130.0, 125.8, 123.5, 123.5, 114.2, 74.7, 68.9, 63.0, 52.0, 43.7, 41.6, 40.9, 39.9, 38.6, 38.4, 37.2, 34.1, 31.4, 30.3, 28.8, 27.9, 21.9, 21.5, 21.4, 19.5, HRMS (FAB+): Calculated: , Found: Experimental details on metathesis assays 2-1. Representative Procedure for RCM of 5 S4 In a glove box, a 2.0 ml volumetric flask was charged with 4b (6.7 mg, 10 µmol) and C 6 D 6 was added to prepare 2.0 ml of stock solution (0.005 M). The stock solution (800 µl, 4.0 µmol) was added into an NMR tube with a screw-cap septum top. The sample was equilibrated at 70 o C in the NMR probe before 5 (19.3 µl, 19.2 mg, 80 µmol) was added via syringe. Data points were collected over an appropriate period of time using the Varian array function. The conversion of 5 to 6 was determined by comparing the ratio of the integrals of the methylene protons in the starting material with those in the product in the 1 H NMR spectra. S3

4 2-2. Representative Procedure for ROMP of 7 A 10 ml volumetric flask was charged with 7 (269 mg, 2.85 mmol) and C 6 D 6 was added to prepare 10.0 ml of stock solution (0.285 M). In a glove box, 4b (1.4 mg, 2.1 µmol) and C 6 D 6 (100 µl ) were added into an NMR tube with a screw-cap septum top. The stock solution (700 µl, 18.8 mg, 200 µmol) was added via syringe and the sample was vigorously shaken for 30 seconds. Then the sample was allowed to stand for 30 min at 23 o C and analyzed by 1 H NMR. The conversion of 7 to 8 and the ratio of cis- and trans-carbon-carbon double bonds in 8 were determined by comparing the ratio of the integrals of the olefinic protons in the starting material with those in the product in the 1 H NMR spectrum Representative Procedure for CM of 9 and Preparation of a substrate mixture In a glove box, tridecane (92.0 µl, 69.6 mg, 377 µmol), 9 (100 µl, 89.2 mg, 755 µmol) and 10 (240 µl, 259 mg, 1.51 mmol) were combined in a 5 ml vial with a screw-cap septum top and a magnetic stir bar. Then the mixture was allowed to stir for 5 min to prepare a substrate mixture Preparation of reaction solution and CM In a glove box, a 5 ml vial with a screw-cap septum top and a magnetic stir bar was charged with 4b (6.7 mg, 10 µmol) and C 6 H 6 (1.0 ml). The catalyst solution was removed from the glove box and then stirred at 70 o C for 10 min under argon. To the catalyst solution, the substrate mixture (115 µl; tridecane: 24.5 µl, 18.5 mg, 100 µmol; 9: 26.6 µl, 23.7 mg, 201 µmol; 10: 63.9 µl, 69.0 mg, 401 µmol) was added via syringe. The reaction solution was allowed to stir at 70 o C and reaction aliquots (ca. 40 µl) were taken at the specific time periods Preparation of reaction solution and CM under reflux In a glove box, a 5 ml flask equipped with a condenser, a 3-way stopcock and a magnetic stir bar was charged with 4b (6.7 mg, 10 µmol), THF (1.0 ml) and the substrate mixture (115 µl; tridecane: 24.5 µl, 18.5 mg, 100 µmol; 9: 26.6 µl, 23.7 mg, 201 µmol; 10: 63.9 µl, 69.0 mg, 401 µmol). The reaction solution was removed from the glove box and then allowed to stir under reflux for 4 h. After cooling to room temperature, reaction aliquot (ca. 40 µl) was taken for GC analysis GC analysis Samples for GC analysis were obtained by adding the reaction aliquot to 400 µl of a 3 M solution of ethyl vinyl ether in isopropyl alcohol. The sample was shaken and allowed to stand for 10 min. Then 100 µl of 1 M slurry of tris(hydroxymethyl)phosphine in isopropyl alcohol was added. S5 The sample was heated at 50 o C for 30 min, cooled to room temperature, passed through pad of silica gel using CH 2 Cl 2 as an eluent and then analyzed via GC. GC response factor and retention time for each substrate were summarized in Table S3. Concentrations of the substrates in each sample were determined by reported method using the response factors. S CM of 9 and 10 in a synthetic scale In a glove box, a 10 ml flask equipped with a condenser, a 3-way stopcock and a magnetic stir bar was charged with 4b (33.9 mg, 50.5 µmol), THF (2.5 ml), degassed H 2 O (2.5 ml), 9 (133 µl, 119mg, 1.00 mmol) and 10 (319 µl, 345 mg, 2.00 mmol). The reaction solution was removed from the glove box and then allowed to stir under reflux for 4 h. Then the reaction solution was cooled to room temperature, evaporated and chromatographed through silica gel (20g, hexane : ethyl acetate = 9 : 1). After evaporation of fractions, 11 (Rf = 0.55, 117 mg, 616 µmol, 61.6% yield based on 9) and 12 (Rf = 0.75, mixture with impurities) were obtained as colorless oil, respectively. Ratio of E isomer and Z isomer of the products were determined by GC analysis (11: Figure S8, E/Z = 0.14; 12: Figure S9, E/Z = 0.03). 3. References (S1) Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, (S2) Jafarpour, L.; Hillier, A. C.; Nolan, S. P. Organometallics 2002, 21, (S3) (a) Edwards, D. A.; Harker, R. M.; Mahon, M. F.; Molloy, K. C. Inorg. Chim. Acta 2002, 328, (b) Stromnova, T. A.; Paschenko, D. V.; Boganova, L. I.; Daineko, M. V.; Katser, S. B.; Churakov, A. V.; Kuz mina, L. G.; Howard, J. A. K. Inorg. Chim. Acta 2003, 350, (S4) Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, (S5) Pederson, R. L.; Fellows, I. M.; Ung, T. A.; Ishihara, H.; Hajela, S. P. Adv. Synth. Catal. 2002, 344, Bond length [Å] Ru1 C (8) Ru1 C (1)* Ru1 C (9) Ru1 O (6) Ru1 Cl (2) Ru1 Cl (2) * Atom distance between Ru1 and C12. Figure S1. X-ray crystal structure and selected bond length of 1b are shown. Displacement ellipsoids are drawn at 50% probability. For clarity, hydrogen atoms have been omitted. S4

5 PPM Figure S2. 1 H NMR spectrum of 1b (C 6D 6, 500 MHz). PPM Figure S3. 13 C NMR spectrum of 1b (C 6D 6, MHz). S5

6 PPM Figure S4. 1 H NMR spectrum of 4a (C 6D 6, 500 MHz). PPM Figure S5. 13 C NMR spectrum of 4a (C 6D 6, MHz). S6

7 PPM Figure S6. 1 H NMR spectrum of a reaction mixture containing 3a and 4a (THF-d 8, 300 MHz) PPM Figure S7. 1 H NMR spectrum of 4b (C 6D 6, 500 MHz). S7

8 PPM Figure S8. 13 C NMR spectrum of 4b (C 6D 6, MHz). S8

9 Z-11 E-11 Figure S9. GC spectrum of a mixture of Z-11 and E-11 S9

10 Z-12 E-12 Figure S10. GC spectrum of a mixture of Z-12 and E-12 S10

11 Table S1. Data for RCM of 5 by 4a a time conversion b time conversion b time conversion b time conversion b time conversion b min % min % min % min % min % a The reaction was carried out using 4a (0.80 µmol) and 5 (19.3 µl, 19.2 mg, 80 µmol) in C 6D 6 (800 µl) at 30 o C. b Conversion of 5 to 6 calculated from the ratio of integrals of the methylene protons of 5 and 6 in 1 H NMR spectrum. S11

12 Table S2. Data for RCM of 5 by 4b a time conversion b time conversion b time conversion b time conversion b time conversion b time conversion b min % min % min % min % min % min % a The reaction was carried out using 4b (4.0 µmol) and 5 (19.3 µl, 19.2 mg, 80 µmol) in C 6D 6 (800 µl) at 70 o C. b Conversion of 5 to 6 calculated from the ratio of integrals of the methylene protons of 5 and 6 in 1 H NMR spectrum. S12

13 Table S3. Data for ROMP of 7 a entry catalyst conversion b / % cis : trans c 1 1a : a : b : 32 a All reactions were carried out using 2 µmol of catalyst and 200 µmol of 7 in 800 µl of C 6D 6 at 23 o C for 30 min. b Calculated from signals in 1 H NMR spectrum. c Ratio of cis- and trans-carbon-carbon double bonds in the product calculated from signals in 1 H NMR spectrum. Table S4. GC response factors and retention times a compound response factor b retension time [min] tridecane Z E Z E Z E a Instrument conditions were as follows; Inlet temperature: 250 o C, detector temperature: 250 o C, hydrogen flow: 32 ml/min, air flow: 400 ml/min, constant col + makeup flow: 30 ml/min. GC Method was as follows; 50 o C for 5 min, followed by a temperature increase of 10 o C/min to 240 o C and a subsequent isothermal period at 240 o C for 5 min (total run time = 29 min). Response factors and retention times are instrument dependent; values may vary on alternate machines. b Determined by reported method. Table S5. Data for CM of 9 and 10 by 4a a time conversion b E /Z c conversion b E /Z c min % % a The reaction was carried out using 4a (3.3 mg, 5.0 µmol), 9 (0.20 mmol), 10 (0.40 mmol) and tridecane (0.10 mmol) in 1.0 ml of C 6H 6 at 23 o C. b Conversion of 9 to the product determined by GC analysis. c Molar ratio of E isomer and Z isomer of the product determined by GC analysis. S13

14 Table S6. Data for CM of 9 and 10 by 4b a time conversion b E /Z c conversion b E /Z c min % % a The reaction was carried out using 4b (6.7 mg, 10 µmol), 9 (0.20 mmol), 10 (0.40 mmol) and tridecane (0.10 mmol) in 1.0 ml of C 6H 6 at 70 o C. b Conversion of 9 to the product determined by GC analysis. c Molar ratio of E isomer and Z isomer of the product determined by GC analysis. Table S7. Data for CM of 9 and 10 by 1a a time conversion b E /Z c conversion b E /Z c min % % a The reaction was carried out using 1a (3.2 mg, 5.1 µmol), 9 (0.20 mmol), 10 (0.40 mmol) and tridecane (0.10 mmol) in 1.0 ml of C 6H 6 at 23 o C. b Conversion of 9 to the product determined by GC analysis. c Molar ratio of E isomer and Z isomer of the product determined by GC analysis. Table S8. Data for CM of 9 and 10 by 1b a time conversion b E /Z c conversion b E /Z c min % % NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d NA d a The reaction was carried out using 1b (3.2 mg, 5.0 µmol), 9 (0.20 mmol), 10 (0.40 mmol) and tridecane (0.10 mmol) in 1.0 ml of C 6H 6 at 23 o C. b Conversion of 9 to the product determined by GC analysis. c Molar ratio of E isomer and Z isomer of the product determined by GC analysis. d GC signal of 12 was too small to quantify. S14

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