Asymmetric H/D exchange reaction of fluorinated aromatic ketones
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1 Asymmetric H/D exchange reaction of fluorinated aromatic ketones Yujun Zhao 1 Xiaozhi Lim 2 Yuanhang Pan 1 Lili Zong 1 Wei Feng 1 and Choon-Hong Tan 1 * Kuo-Wei Huang 2 * 1 Department of Chemistry and MedChem Program, 3 Science Drive 3, National University of Singapore, Singapore ; chmtanch@nus.edu.sg 2 King Abdullah University of Science and Technology (KAUST), Division of Chemicals and Life Sciences & Engineering and KAUST Catalysis Center, Thuwal , Saudi Arabia hkw@kaust.edu.sa 1 P a g e
2 Supporting Information General procedures and method 3 Typical experimental procedure for deuteration of 1a 4 1H NMR and HPLC spectrum 6 Density Functional Theory (DFT) computational details 8 Chemical Kinetics Simulation results 15 2 P a g e
3 General procedures and methods 1 H and 13 C NMR spectra were recorded on a Bruker ACF300 (300MHz), Bruker DPX300 (300MHz) or AMX500 (500MHz) spectrometer. Chemical shifts are reported in parts per million (ppm). The residual solvent peak was used as an internal reference. Low resolution mass spectra were obtained on a Finnigan/MAT LCQ spectrometer in ESI mode and a Finnigan/MAT 95XL-T mass spectrometer in FAB mode. All high resolution mass spectra were obtained on a Finnigan/MAT 95XL-T spectrometer. Enantiomeric excess values were determined by chiral HPLC analysis on two sets: Jasco HPLC units, including a Jasco DG Degasser, a LG Ternary Gradient Unit, a PU-980 Intelligient HPLC Pump, UV-975 Intelligient UV/VIS Detectors, and an AS-950 Intelligient Sampler; Dionex Ultimate 3000 HPLC units, including a Ultimate 3000 Pump, Ultimate 3000 variable Detectors. Optical rotations were recorded on Jasco DIP-1000 polarimeter. Analytical thin layer chromatography (TLC) was performed with Merck pre-coated TLC plates, silica gel 60F-254, layer thickness 0.25 mm. Flash chromatography separations were performed on Merck 60 ( mm) mesh silica gel. Dichloromethane was distilled from CaH 2 and stored under N 2 atmosphere. Other reagents and solvents were commercial grade and were used as supplied without further purification, unless otherwise stated. 3 P a g e
4 Typical experimental procedure for deuteration of 1a. To a solution of 30 mol% chiral guanidine 2 (2.7 mg, mmol) in 0.8 ml of ClCH 2 CH 2 Cl (DCE), D 2 O (0.12 ml, 6 mmol) was added. Then, the reaction mixture was cooled to 0 o C. After stirring at 0 o C for 20 min, 1a (9.7 mg, 0.04 mmol) was added in two batches. This resulting solution was stirred for 15 hours at 0 o C. The reaction mixture was purified by flash chromatography on silica gel eluting with hexane/ea (30/1 to 5/1) to give 1a-d 1 (13 mg) as an off-white solid with 96% yield. The deuteration incorporation was determined by 1 H NMR spectroscopy by comparing the relative intensity to a non-exchangeable proton in the molecule. The product 1a-d 1 was obtained as an off-white solid. Yield: 96%. ee: 24%; 100%D 1 H NMR (500 MHz, CDCl 3, ppm): δ = 8.2 (s, 1H), 7.63 (d, J = 8.2 Hz, 1H), 7.16 (d, J = 8.2 Hz, 1H), (m, 2H), (m, 1H), (m, 1H) The ee was determined by HPLC analysis. PHENOMENEX Lux 5u Amylose-2 (4.6 mm i.d. x 250 mm, 4.6 mm i.d. x 250 mm); Hexane/2-propanol = 95/5; flow rate 0.5 ml/min; 25 C; 254 nm; retention time: major isomer: 50.0 min; minor isomer: 46.8 min 4 P a g e
5 The product 1b-d 1 was obtained as white solid. Yield: 98%. ee: 30%; 95%D 1 H NMR (300 MHz, CDCl 3, ppm): δ = 7.97 (d, J = 8.6 Hz, 1H), 7.73 (d, J = 8.3 Hz, 1H), 7.34(d, J = 8.1 Hz, 2H), (m, 1H), (m, 2H), (m, 5H) The ee was determined by HPLC analysis. PHENOMENEX Lux 5u Amylose-2 (4.6 mm i.d. x 250 mm, 4.6 mm i.d. x 250 mm); Hexane/2-propanol = 92/8; flow rate 0.8 ml/min; 25 C; 254 nm; retention time: major isomer: min; minor isomer: min 5 P a g e
6 1H NMR and HPLC spectrum 6 P a g e
7 7 P a g e
8 DFT computational details DFT calculations were performed using the Gaussian 09 program. 1 Becke 2 three parameter functional with the non local Lee-Yang-Parr 3 correlation functional (B3LYP) theory was applied with 6-31G(d) Pople basis set 4 for all atoms. Cartesian coordinates and thermodynamic data for transition states presented S-H 2 O-TS Imaginary Frequency= cm -1 Zero-point correction= (Hartree/Particle) Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= C C C C H H H N N N H C O Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Comperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz J. C., J. V.; Fox, D. J. 2009, Gaussian. 2 Becke, A. D. J. Chem. Phys. 1983, 98, Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724. (b) Hariharan, P. C.; Pople, J. A. Theo. Chem. Acc. 1973, 28, 213. (c) Hehre, W.J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, P a g e
9 H H H C C C C C C C H H C C H H H F C H H O H H H H C C H H H C H H H C H H H C C H H H P a g e
10 C H H H C H H H R-H 2 O-TS Imaginary Frequency= cm -1 Zero-point correction= (Hartree/Particle) Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= C C C C H H H N N N H H H C C C O H H H C C C C C C C H P a g e
11 H C C H H H C H H H C H H H C H H H C H H H C H H H C H H H F C H H O H H S -TS Imaginary Frequency= cm -1 Zero-point correction= (Hartree/Particle) Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= P a g e
12 C C C C H H H H N N N H H H C C C C H H H C H H H C H H H C H H H C H H H C H H H O C C P a g e
13 C C C H C F H C C C H H C H H H H H R -TS Imaginary Frequency= cm -1 Zero-point correction= (Hartree/Particle) Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= C C C C H H H H N N N H C O C C C C C P a g e
14 H C F H C C C H H C H H H H H C C H H H C H H H C H H H C C H H H C H H H C H H H H H P a g e
15 Computer Simulations by CKS Reaction conditions: A: 1 M B: 1 M C: 0 M D: 0 M Kinetic Isotope Effect = 7 Catalyst Selectivity = 20:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-prod uct overall ee ee of D-Product % 0.0% NA % 0.0% 88.6% % -0.1% 88.9% % 0.1% 89.6% % 0.3% 89.7% % 0.6% 89.4% % 1.1% 89.4% % 1.7% 88.7% % 2.7% 88.4% % 4.6% 87.7% % 7.8% 86.6% % 13.8% 84.9% % 20.7% 82.3% % 26.5% 79.0% % 35.2% 75.3% % 41.3% 70.4% % 45.2% 65.3% % 46.9% 57.5% % 45.7% 53.1% % 42.9% 48.2% % 39.2% 42.0% % 34.9% 36.2% % 20.0% 20.2% 15 P a g e
16 Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 7 and catalyst selectivity of 20 to 1. Kinetic Isotope Effect = 7 Catalyst Selectivity = 10:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % 0.2% 83.5% % 0.3% 82.4% % 0.1% 80.1% % 0.3% 80.1% % 0.2% 78.8% % 0.6% 78.8% % 1.1% 79.2% % 1.8% 79.5% % 2.8% 79.6% % 4.7% 79.5% % 6.9% 78.4% % 11.1% 77.7% % 16.1% 75.7% % 22.0% 72.7% 16 P a g e
17 % 28.3% 70.2% % 34.5% 67.5% % 38.2% 64.0% % 41.4% 60.7% % 43.6% 54.0% % 42.3% 49.2% % 38.2% 41.4% % 33.2% 34.6% % 15.1% 15.1% Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 7 and catalyst selectivity of 10 to 1. Kinetic Isotope Effect = 7 Catalyst Selectivity = 5:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % 0.3% 71.9% % 0.4% 69.0% % 0.7% 66.6% % 1.3% 66.2% 17 P a g e
18 % 1.6% 64.8% % 2.9% 65.8% % 4.0% 65.4% % 4.9% 64.5% % 6.6% 63.8% % 8.8% 63.5% % 11.2% 62.7% % 14.1% 61.3% % 17.4% 59.1% % 21.6% 57.6% % 26.3% 56.2% % 29.5% 53.4% % 33.9% 49.8% % 35.5% 44.9% % 35.3% 41.7% % 31.8% 34.5% % 27.5% 28.4% % 14.5% 14.6% Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 7 and catalyst selectivity of 5 to 1. Kinetic Isotope Effect = 7 Catalyst Selectivity = 2:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: P a g e
19 Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % -0.4% 21.9% % -0.7% 25.0% % -0.4% 28.2% % 0.2% 31.3% % 0.7% 32.2% % 1.3% 31.9% % 1.9% 31.7% % 2.5% 31.7% % 3.2% 32.0% % 4.1% 31.2% % 5.2% 31.7% % 6.5% 31.5% % 7.2% 31.3% % 8.6% 29.9% % 10.4% 28.8% % 11.5% 28.5% % 13.6% 26.9% % 15.1% 26.6% % 16.9% 25.0% % 17.7% 22.7% % 17.8% 21.6% % 16.8% 18.2% % 10.0% 10.1% Kinetic Isotope Effect = 5 Catalyst Selectivity = 20:1 Reaction Scheme: 19 P a g e
20 A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % -0.2% 88.3% % 0.0% 89.5% % 0.2% 89.4% % 0.4% 89.0% % 0.7% 89.1% % 1.1% 88.6% % 1.5% 87.5% % 2.9% 86.9% % 5.0% 86.0% % 9.4% 84.8% % 14.9% 82.1% % 19.9% 78.1% % 27.5% 73.6% % 32.0% 70.6% % 34.6% 66.8% % 37.0% 63.4% % 39.0% 60.0% % 39.9% 54.4% % 38.3% 48.3% % 36.0% 42.3% % 31.9% 35.2% % 22.8% 23.9% % 10.1% 10.2% 20 P a g e
21 Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 5 and catalyst selectivity of 20 to 1. Kinetic Isotope Effect = 5 Catalyst Selectivity = 10:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % 0.2% 83.5% % 0.3% 82.4% % 0.0% 79.9% % 0.3% 80.1% % 0.1% 78.7% % 0.4% 78.4% % 1.1% 78.9% % 1.8% 79.1% % 2.8% 79.2% % 3.8% 79.1% % 5.1% 78.5% % 6.4% 77.5% % 8.6% 76.9% 21 P a g e
22 % 11.2% 75.9% % 14.4% 74.4% % 20.6% 69.7% % 27.6% 65.9% % 32.2% 61.0% % 35.4% 56.3% % 36.9% 51.0% % 36.5% 48.1% % 33.3% 39.4% % 31.0% 34.6% % 24.8% 26.6% % 8.9% 8.9% Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 5 and catalyst selectivity of 10 to 1. Kinetic Isotope Effect = 5 Catalyst Selectivity = 5:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % 0.3% 70.2% 22 P a g e
23 % 0.8% 68.2% % 0.8% 66.0% % 1.4% 64.9% % 2.0% 64.9% % 3.0% 65.2% % 4.1% 64.4% % 5.6% 63.6% % 7.1% 62.8% % 9.5% 62.3% % 11.5% 61.1% % 13.7% 58.8% % 16.7% 56.6% % 20.4% 54.9% % 23.5% 52.7% % 25.9% 49.8% % 28.1% 47.2% % 29.7% 44.3% % 30.3% 41.4% % 28.0% 34.2% % 26.7% 30.4% % 21.8% 23.3% % 10.7% 10.8% Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 5 and catalyst selectivity of 5 to 1. Kinetic Isotope Effect = 5 Catalyst Selectivity = 2:1 Reaction Scheme: 23 P a g e
24 A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % -0.7% 24.6% % -0.4% 28.5% % -0.2% 30.2% % 0.5% 31.3% % 1.1% 31.5% % 1.3% 31.2% % 2.2% 31.1% % 3.6% 31.2% % 4.6% 31.7% % 5.7% 31.4% % 6.3% 30.7% % 6.7% 29.1% % 7.9% 28.2% % 9.7% 27.9% % 11.0% 27.0% % 12.6% 25.9% % 13.7% 24.6% % 14.5% 23.0% % 14.5% 22.0% % 15.2% 20.6% % 14.0% 16.8% % 13.2% 14.6% % 7.7% 7.8% 24 P a g e
25 Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 5 and catalyst selectivity of 2 to 1. Kinetic Isotope Effect = 3 Catalyst Selectivity = 20:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d-product overall ee ee of D-Product % 0.0% NA % -0.2% 88.0% % -0.1% 89.1% % 0.1% 89.4% % 0.3% 88.8% % 0.6% 88.8% % 1.0% 88.3% % 1.5% 87.3% % 2.7% 86.4% % 4.2% 84.9% % 7.6% 83.0% % 11.5% 79.5% % 15.1% 75.0% % 18.3% 70.6% 25 P a g e
26 % 21.6% 66.9% % 23.9% 63.1% % 26.2% 55.4% % 26.9% 49.5% % 27.0% 44.5% % 25.8% 39.1% % 25.1% 35.1% % 22.3% 28.9% % 17.1% 20.0% % 11.8% 13.1% % 5.2% 5.3% Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 3 and catalyst selectivity of 20 to 1. Kinetic Isotope Effect = 3 Catalyst Selectivity = 10:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d- Product overall ee ee of D-Product % 0.0% NA % 0.2% 83.3% % -0.1% 78.7% % 0.1% 79.6% % 0.1% 77.6% 26 P a g e
27 % 0.6% 78.0% % 1.6% 78.5% % 2.5% 77.8% % 4.1% 77.2% % 5.4% 75.9% % 8.0% 74.7% % 10.3% 72.2% % 12.7% 68.6% % 16.0% 65.2% % 20.9% 60.8% % 22.4% 54.3% % 24.4% 49.3% % 25.0% 44.3% % 23.3% 36.8% % 23.1% 33.1% % 21.4% 27.9% % 16.5% 19.7% % 11.3% 12.6% % 4.9% 5.0% Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 3 and catalyst selectivity of 10 to 1. Kinetic Isotope Effect = 3 Catalyst Selectivity = 5:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: P a g e
28 Table of selected values: Time /h [A] [B] [C] [D] d- Product overall ee ee of D-Product % 0.0% NA % 0.4% 70.2% % 0.7% 66.4% % 1.0% 65.2% % 2.0% 64.6% % 3.2% 64.3% % 4.0% 64.0% % 4.0% 62.5% % 4.6% 61.4% % 5.4% 61.0% % 6.5% 60.6% % 7.7% 60.2% % 9.8% 56.0% % 12.3% 53.1% % 15.5% 50.8% % 17.2% 46.9% % 18.9% 43.2% % 20.1% 39.5% % 20.6% 34.4% % 20.2% 29.8% % 19.1% 25.5% % 15.0% 17.7% % 11.4% 12.6% % 5.0% 5.1% 28 P a g e
29 Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 3 and catalyst selectivity of 5 to 1. Kinetic Isotope Effect = 3 Catalyst Selectivity = 2:1 Reaction Scheme: A -> C Rate constant: A -> D Rate constant: B -> C Rate constant: B -> D Rate constant: C <=> D Rate constant: Table of selected values: Time /h [A] [B] [C] [D] d- Product overall ee ee of D-Product % 0.0% NA % -0.8% 24.4% % -0.3% 28.8% % -0.2% 30.3% % 0.3% 30.7% % 0.6% 30.1% % 1.1% 30.1% % 1.4% 29.3% % 2.7% 29.6% % 3.7% 30.3% % 4.6% 29.7% % 5.1% 29.1% % 5.3% 27.8% % 5.6% 26.4% % 6.8% 26.0% % 7.7% 23.9% % 9.6% 21.8% % 10.3% 20.0% % 10.5% 17.8% % 10.2% 15.5% % 8.7% 11.5% % 7.2% 8.5% % 3.9% 4.0% 29 P a g e
30 Graph: Simulation result of asymmetric H/D reaction, assuming kinetic isotope effect of 3 and catalyst selectivity of 2 to P a g e
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