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1 Supporting Information for: Mechanism of N,N,N-Amide Ruthenium(II) Hydride Mediated Acceptorless Alcohol Dehydrogenation: Inner-Sphere β-h Elimination versus Outer-Sphere Bifunctional Metal Ligand Cooperativity Kuei-Nin T. Tseng, Jeff W. Kampf, and Nathaniel K. Szymczak* Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109, United States Corresponding Author: Table of Contents 1PhEtOH dehydrogenation rate dependence on [3] Complete reaction profile of 1PhEtOH dehydrogenation: standard conditions Kinetic profiles for [3] dependence studies (averaged data from three trials) Kinetic profiles for [1PhEtOH] dependence studies (averaged data from three trials) Kinetic profiles for [PPh 3] dependence studies (averaged data from three trials) Kinetic profiles for temperature dependence studies, < 7.5 M 1PhEtOH (averaged data from three trials) Kinetic profiles for temperature dependence studies, > 7.5 M 1PhEtOH (averaged data from three trials) Kinetic profiles for Hammett studies (averaged data from three trials) Kinetic profiles for isotopic labeling studies (averaged data from three trials) Kinetic profiles for 4, 4-Me, and 5 (averaged data from three trials) Kinetic profiles for 7-R (R = H, Me, Cl, OMe, OH) (averaged data from three trials) Kinetic profiles for 7-H and 7-OH with 5 equiv. NaO t Bu (averaged data from three trials) NMR spectra for Ru(HbMepi)(PPh 3)Cl[PF 6] NMR spectra for Ru(b4,6-Mepi)(PPh 3)Cl (4-Me) NMR spectra for Ru(bMepi Me )(PPh 3)OTf 2 (5) S2 S2 S2 S3 S4 S5 S6 S7 S7 S8 S9 S10 S11 S12 S13 NMR spectra for Ru(bMepi)(PPh 3)(OCH 2CF 3) (6) S14-15 NMR spectra for Ru(bpi)(PPh 3) 2Cl (7-H) NMR spectra for Ru(b4Mepi)(PPh 3) 2Cl (7-Me) NMR spectra for Ru(b4Clpi)(PPh 3) 2Cl (7-Cl) NMR spectra for Ru(b4OMepi)(PPh 3) 2Cl (7-OMe) NMR spectra for [Ru(CH 2CH 3pi)(PPh 3)] 2 (8) NMR spectra for Ru(HbMepi)(PPh 3) 2Cl 2 (9) Equilibrium Constants between 3 and Ru(bMepi)(PPh 3)(OCHPhMe) S16 S17 S18 S19 S20 S21 S22 S1
2 Figure S1. 1PhEtOH dehydrogenation rate dependence on [3]. Figure S4. 1PhEtOH dehydrogenation reaction profile: 35 ppm 3. Figure S2. Complete reaction profile of 1PhEtOH dehydrogenation: standard conditions. Figure S5. 1PhEtOH dehydrogenation reaction profile: standard conditions, 100 ppm 3. Figure S3. 1PhEtOH dehydrogenation reaction profile: 23 ppm 3. S2
3 Figure S6. 1PhEtOH dehydrogenation reaction profile: 6.5 M 1PhEtOH. Figure S9. 1PhEtOH dehydrogenation reaction profile: 8.0 M 1PhEtOH. Figure S7. 1PhEtOH dehydrogenation reaction profile: 7.0 M 1PhEtOH. Figure S8. 1PhEtOH dehydrogenation reaction profile: 7.8 M 1PhEtOH. S3
4 Figure S10. 1PhEtOH dehydrogenation reaction profile: 2 equiv. PPh 3. Figure S13. 1PhEtOH dehydrogenation reaction profile: 20 equiv. PPh 3. Figure S11. 1PhEtOH dehydrogenation reaction profile: 5 equiv. PPh 3. Figure S12. 1PhEtOH dehydrogenation reaction profile: 10 equiv. PPh 3. S4
5 Figure S14. 1PhEtOH dehydrogenation reaction profile: 90 C, [1PhEtOH] < 7.5 M. Figure S17. 1PhEtOH dehydrogenation reaction profile: 130 C, [1PhEtOH] < 7.5 M. Figure S15. 1PhEtOH dehydrogenation reaction profile: 100 C, [1PhEtOH] < 7.5 M. Figure S16. 1PhEtOH dehydrogenation reaction profile: 110 C, [1PhEtOH] < 7.5 M. S5
6 Figure S18. 1PhEtOH dehydrogenation reaction profile: 90 C, [1PhEtOH] > 7.5 M. Figure S21. 1PhEtOH dehydrogenation reaction profile: 120 C, [1PhEtOH] > 7.5 M. Figure S19. 1PhEtOH dehydrogenation reaction profile: 1000 C, [1PhEtOH] > 7.5 M. Figure S22. 1PhEtOH dehydrogenation reaction profile: 130 C, [1PhEtOH] > 7.5 M. Figure S20. 1PhEtOH dehydrogenation reaction profile: 110 C, [1PhEtOH] > 7.5 M. S6
7 Figure S23. 1-(4-methylphenyl)ethanol dehydrogenation reaction profile. Figure S26. 1PhEtOD dehydrogenation reaction profile. Figure S24. 1-(4-methoxyphenyl)ethanol dehydrogenation reaction profile. Figure S27. 1PhCH 3CDOH dehydrogenation reaction profile. Figure S28. 1PhCH 3CDOD dehydrogenation reaction profile. Figure S25. 1-(4-fluorophenyl)ethanol dehydrogenation reaction profile. S7
8 Figure S29. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(bMepi)(PPh 3)Cl (4). Figure S32. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(bMepi Me )(PPh 3)OTf 2 (5). Figure S30. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(b4,6-Mepi)(PPh 3)Cl (4-Me). Figure S31. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(bMepi)(PPh 3)Cl (4) and 2 equiv. NaOTf. S8
9 Figure S33. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(bpi)(PPh 3) 2Cl (7-H). Figure S36. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(b4OMepi)(PPh 3) 2Cl (7-OMe). Figure S34. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(b4Mepi)(PPh 3) 2Cl (7-Me). Figure S37. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(b4OHpi)(PPh 3) 2Cl (7-OH). Figure S35. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(b4Clpi)(PPh 3) 2Cl (7-Cl). S9
10 Figure S38. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(bpi)(PPh 3) 2Cl (7-H) with 5 equiv. NaO t Bu. Figure S39. 1PhEtOH dehydrogenation reaction profile catalyzed by Ru(b4OHpi)(PPh 3) 2Cl (7-OH) with 5 equiv. NaO t Bu. S10
11 Figure S40. 1 H NMR (700 MHz, CD 2Cl 2) spectrum for Ru(HbMepi)(PPh 3)Cl[PF 6]. Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(HbMepi)(PPh 3)Cl[PF 6]. Figure S P{ 1 H} NMR (162 MHz, CD 2Cl 2) spectrum for Ru(HbMepi)(PPh 3)Cl[PF 6]. S11
12 Figure S43. 1 H NMR (700 MHz, CD 2Cl 2) spectrum for Ru(b4,6-Mepi)(PPh 3)Cl (4-Me). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(b4,6-Mepi)(PPh 3)Cl (4-Me). Figure S P{ 1 H} NMR (162 MHz, C 6D 6) spectrum for Ru(b4,6-Mepi)(PPh 3)Cl (4-Me). S12
13 Figure S46. 1 H NMR (700 MHz, CD 2Cl 2) spectrum for Ru(bMepi Me )(PPh 3)OTf 2 (5). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(bMepi Me )(PPh 3)OTf 2 (5). Figure S P{ 1 H} NMR (202 MHz, CD 2Cl 2) spectrum for Ru(bMepi Me )(PPh 3)OTf 2 (5). S13
14 Figure S49. 1 H NMR (700 MHz, C 6D 6) spectrum for Ru(bMepi)(PPh 3)(OCH 2CF 3) (6). Figure S C{ 1 H} NMR (176 MHz, C 6D 6) spectrum for Ru(bMepi)(PPh 3)(OCH 2CF 3) (6). Figure S P{ 1 H} NMR (283 MHz, PhMe-d 8) spectrum for Ru(bMepi)(PPh 3)(OCH 2CF 3) (6). S14
15 Figure S F NMR (376 MHz, C 6D 6) spectrum for Ru(bMepi)(PPh 3)(OCH 2CF 3) (6). S15
16 Figure S53. 1 H NMR (700 MHz, CD 2Cl 2) spectrum for Ru(bpi)(PPh 3) 2Cl (7-H). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(bpi)(PPh 3) 2Cl (7-H). Figure S P{ 1 H} NMR (162 MHz, C 6D 6) spectrum for Ru(bpi)(PPh 3) 2Cl (7-H). S16
17 Figure S56. 1 H NMR (700 MHz, CD 2Cl 2) spectrum for Ru(b4Mepi)(PPh 3) 2Cl (7-Me). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(b4Mepi)(PPh 3) 2Cl (7-Me). Figure S P{ 1 H} NMR (162 MHz, C 6D 6) spectrum for Ru(b4Mepi)(PPh 3) 2Cl (7-Me). S17
18 Figure S59. 1 H NMR (400 MHz, C 6D 6) spectrum for Ru(b4Clpi)(PPh 3) 2Cl (7-Cl). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(b4Clpi)(PPh 3) 2Cl (7-Cl). Figure S P{ 1 H} NMR (162 MHz, C 6D 6) spectrum for Ru(b4Clpi)(PPh 3) 2Cl (7-Cl). S18
19 Figure S62. 1 H NMR (700 MHz, CD 2Cl 2) spectrum for Ru(b4OMepi)(PPh 3) 2Cl (7-OMe). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(b4OMepi)(PPh 3) 2Cl (7-OMe). Figure S P{ 1 H} NMR (162 MHz, C 6D 6) spectrum for Ru(b4OMepi)(PPh 3) 2Cl (7-OMe). S19
20 Figure S65. 1 H NMR (700 MHz, C 6D 6) spectrum for [Ru(CH 2CH 3pi)(PPh 3)] 2 (8). Figure S C{ 1 H} NMR (176 MHz, C 6D 6) spectrum for [Ru(CH 2CH 3pi)(PPh 3)] 2 (8). Figure S P{ 1 H} NMR (283 MHz, C 6D 6) spectrum for [Ru(CH 2CH 3pi)(PPh 3)] 2 (8). S20
21 Figure S68. 1 H NMR (400 MHz, CD 2Cl 2) spectrum for Ru(HbMepi)(PPh 3) 2Cl 2 (9). Figure S C{ 1 H} NMR (176 MHz, CD 2Cl 2) spectrum for Ru(HbMepi)(PPh 3) 2Cl 2 (9). Figure S P{ 1 H} NMR (162 MHz, CD 2Cl 2) spectrum for Ru(HbMepi)(PPh 3) 2Cl 2 (9). S21
22 Table S1. Equilibrium Constants between 3 and Ru(bMepi)(PPh 3 )(OCHPhMe) Entry [1PhEtOH] (M) Ratio of 3 to alkoxide K eq : : : S22
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