Nickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol

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1 Nickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol Ailing Zhang, Sakthi Raje, Jianguo Liu, Xiaoyan Li, Raja Angamuthu, Chen-Ho Tung, and Wenguang Wang* School of Chemistry and Chemical Engineering, Shandong University, Jinan, , China Laboratory of Inorganic Synthesis and Bioinspired Catalysis (LISBIC), Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur , India Figure S1. 1 H NMR spectrum of [1](BF 4 ) 2... p S2 Figure S2. 31 P { 1 H} NMR spectrum of [1](BF 4 ) 2... p S3 Figure S3. ESI-MS spectrum of [1](BF 4 ) 2... p S4 Figure S4. ESI-MS spectrum of [1(NCMe) 2 ](BF 4 ) 2... p S5 Figure S5. 1 H NMR spectrum of [1-H]BF 4... p S6 Figure S6. 31 P { 1 H} NMR spectrum of [1-H]BF 4... p S7 Figure S7. ESI-MS spectrum of [1-H]BF 4... p S8 Figure S8. Crystal structure of [1-H]BF 4... p S9 Figure S9. 1 H NMR spectrum of [1] 0... p S10 Figure S P { 1 H} NMR spectrum of [1] 0... p S11 Figure S11. 1 H NMR spectrum of [1-CH 3 ]BPh 4... p S12 Figure S P { 1 H} NMR spectrum of [1-CH 3 ]BPh 4... p S13 Figure S C NMR spectrum of [1-CH 3 ]BPh 4... p S14 Figure S14. ESI-MS spectrum of [1-CH 3 ]BPh 4... p S15 Figure S15. 2 H NMR spectrum of [1-CD 3 ]BPh 4... p S16 Figure S P { 1 H} NMR spectrum of [1-CD 3 ]BPh 4... p S17 Figure S17. ESI-MS spectrum of [1-CD 3 ]BPh 4... p S18 Figure S18. 1 H NMR spectrum of [1-COCH 3 ]BPh 4... p S19 Figure S P { 1 H} NMR spectrum of [1-COCH 3 ]BPh 4... p S20 Figure S C NMR spectrum of [1-COCH 3 ]BPh 4... p S21 Figure S21. ESI-MS spectrum of [1-COCH 3 ]BPh 4... p S22 Figure S22. 2 H NMR spectrum of [1-COCD 3 ]BPh 4... p S23 Figure S P { 1 H} NMR spectrum of [1-COCD 3 ]BPh 4... p S24 Figure S C NMR spectrum of [1-COCD 3 ]BPh 4... p S25 Figure S25. ESI-MS spectrum of [1-COCD 3 ]BPh 4... p S26 Figure S26. IR spectra of [1-COCD 3 ]BPh 4 and [1-COCH 3 ]BPh 4... p S27 Figure S27. IR spectra recorded for the reaction of [1-COCH 3 ]BPh 4 and NBu 4 BH 4... p S28 Figure S28. 2 H NMR spectra of CD 3 CHO and CD 3 CH 2 OH... p S29 Figure S29. 1 H NMR spectrum of [1-CO] 0... p S30 Figure S P { 1 H} NMR spectrum of [1-CO] 0... p S31 Table S1-S6. Crystal data and structure refinement parameters p S32-S38 S1

2 Figure S1. 1 H NMR spectrum of [1](BF 4 ) 2 in CD 2 Cl 2. S2

3 Figure S2. 31 P NMR spectrum of [1](BF 4 ) 2 in CD 2 Cl 2. S3

4 Figure S3. ESI-MS spectrum of [1](BF 4 ) 2. S4

5 Figure S4. ESI-MS spectrum of [1(NCMe) 2 ](BF 4 ) 2. S5

6 Figure S5. 1 H NMR spectrum of [1-H]BF 4 in CD 3 CN. S6

7 Figure S6. 31 P NMR spectrum of ([1-H]BF 4 in CD 3 CN. S7

8 Figure S7. ESI-MS spectrum for [1-H]BF 4. S8

9 Figure S8. Molecular Structure (50% probability thermal ellipsoids) of [1-H]BF 4. For clarity, the BF 4 - counter anions are not shown and hydrogen atoms except for the hydride ligand are omitted. Selected distances (Å) and angles (deg): [1-H] +, Ni1-S (9), 2.339(1), Ni1-P 2.139(1), 2.146(1), S1-Ni1-S (4), P1-Ni1-S (4), P1-Ni1-S (4), P1-Ni1-P (4), P2-Ni1-S (3), P2-Ni1-S (4). S9

10 Figure S9. 1 H NMR spectrum of [1] 0 in C 6 D 6. S10

11 Figure S P NMR spectrum of [1] 0 in C 6 D 6. S11

12 Figure S11. 1 H NMR spectrum of [1-CH 3 ]BPh 4 in CD 2 Cl 2. S12

13 Figure S P NMR spectrum of [1-CH 3 ]BPh 4 in CD 2 Cl 2. S13

14 Figure S C NMR spectrum of [1-CH 3 ]BPh 4 in CD 2 Cl 2. S14

15 Figure S14. ESI-MS spectrum of [1-CH 3 ]BPh 4. S15

16 Figure S15. 2 H NMR spectrum of [1-CD 3 ]BPh 4 in CH 2 Cl 2. S16

17 Figure S P NMR spectrum of [1-CD 3 ]BPh 4 in CD 2 Cl 2. S17

18 Figure S17. ESI-MS spectrum of [1-CD 3 ]BPh 4. S18

19 Figure S18. 1 H NMR spectrum of [1-COCH 3 ]BPh 4 in CD 2 Cl 2. S19

20 Figure S P NMR spectrum of [1-COCH 3 ]BPh 4 in CD 2 Cl 2. S20

21 Figure S C NMR spectrum of [1-COCH 3 ]BPh 4 in CD 2 Cl 2. S21

22 Figure S21. ESI-MS spectrum of [1-COCH 3 ]BPh 4. S22

23 Figure S22. 2 H NMR spectrum of [1-COCD 3 ]BPh 4 in CH 2 Cl 2. S23

24 Figure S P NMR spectrum of [1-COCD 3 ]BPh 4 in CD 2 Cl 2. S24

25 Figure S C NMR spectrum of [1-COCD 3 ]BPh 4 in CD 2 Cl 2. S25

26 Figure S25. ESI-MS spectrum of [1-COCD 3 ]BPh 4. S26

27 Figure S26. IR spectra (ν CO region) of [1-COCH 3 ]BPh 4 and [1-COCD 3 ]BPh 4 in CH 2 Cl 2 solution. Result: [1-COCD 3 ]BPh 4, ν CO (cm -1, CH 2 Cl 2 ), [1-COCH 3 ]BPh 4, ν CO (cm -1, CH 2 Cl 2 ), S27

28 Figure S27. IR spectra for (a) [1-COCH 3 ]BPh 4 in MeCN solution, (b) the reaction of [1-COCH 3 ]BPh 4 and NBu 4 BH 4 in MeCN solution. Results: a) ν CO (cm -1, CH 3 CN), b) ν CO (cm -1, CH 3 CN), 1907, S28

29 Figure S28. 2 H NMR spectra of CD 3 CHO and CD 3 CH 2 OH produced by the reaction of [1-COCH 3 ]BPh 4 with two equiv of NBu 4 BH 4 in THF. Note: 1 µl of H 2 O was added to the mixture to quench the reaction before conducting NMR analysis S29

30 Figure S29. 1 H NMR spectrum of [1-CO] 0 in CD 3 CN. S30

31 Figure S P NMR spectrum of [1-CO] 0 in CD 3 CN. S31

32 X-ray Crystallography Single crystals with appropriate dimensions were chosen under an optical microscope and quickly coated with high vacuum grease (Dow Corning Corporation) to prevent decomposition. Intensity data and cell parameters were recorded at 173 K on a Bruker Apex II single crystal diffractometer, employing a Mo K α radiation (λ = Å) and a CCD area detector. The raw frame data were processed using SAINT and SADABS to yield the reflection data file. 1 The structure was solved using the charge-flipping algorithm, as implemented in the program SUPERFLIP 2 and refined by full-matrix least-squares techniques against F 2 o using the SHELXL program 3 through the OLEX2 interface. 4 Hydrogen atoms at carbon were placed in calculated positions and refined isotropically by using a riding model. Appropriate restraints or constraints were applied to the geometry and the atomic displacement parameters of the atoms in the cluster. All structures were examined using the Addsym subroutine of PLATON 5 to ensure that no additional symmetry could be applied to the models. Pertinent crystallographic data collection and refinement parameters are collated in Table S1-S6. Reference: 1. APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, Sheldrick, G. M. Acta. Cryst. Sect. C 2015, 71, Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42, Spek, A. L. Acta Cryst. Sect. D 2009, 65, S32

33 Table S1: Crystal data and structure refinement parameters for [1](BF 4 ) 2 Empirical formula C 40 H 36 B 2 F 8 NiP 2 S 2 Formula weight Crystal system monoclinic Space group P 2 1 /c Unit cell dimensions a = 9.106(3) Å b = (7) Å c = (7) Å α = 90 β = (3) γ = 90 Volume 3819(2) Å 3 Z 4 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) 1792 Crystal size mm 3 Theta range for data collection 4.98 to 50 Index ranges -10 h 10, -23 k 23, -18 l 25 Reflections collected Independent reflections 6731 [R(int) = ] Completeness to theta = % Absorption correction multi-scan Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 6731/0/496 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 S33

34 Table S2: Crystal data and structure refinement parameters for [1(NCMe) 2 ](BF 4 ) 2 Empirical formula C 26 H 31 BF 4 NNi 0.50 OPS Formula weight Crystal system monoclinic Space group C 2/c Unit cell dimensions a = (4) Å b = (15) Å c = (2) Å α = 90 β = (10) γ = 90 Volume (12) Å 3 Z 8 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) Crystal size mm 3 Theta range for data collection to Index ranges -34 h 34, -14 k 14, -23 l 23 Reflections collected Independent reflections 5044 [R(int) = ] Completeness to theta = % Absorption correction multi-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 5044/0/324 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 S34

35 Table S3: Crystal data and structure refinement parameters for [1-H]BF 4 Empirical formula C 40 H 37 BF 4 NiP 2 S 2 Formula weight Crystal system triclinic Space group P -1 Unit cell dimensions a = (8) Å b = (11) Å c = (12) Å α = (4) β = (4)(10) γ = (4) Volume (3) Å 3 Z 2 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) Crystal size mm 3 Theta range for data collection 5.52 to Index ranges -13 h 13, -17 k 17, -18 l 18 Reflections collected Independent reflections 7328 [R(int) = ] Completeness to theta = % Absorption correction multi-scan Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 7328/0/455 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 S35

36 Table S4: Crystal data and structure refinement parameters for [1-CH 3 ] BPh 4 Empirical formula C 66 H 61 BCl 2 NiP 2 S 2 Formula weight Crystal system triclinic Space group P -1 Unit cell dimensions a = (7) Å b = (11) Å c = (15) Å α = (5) β = (5) γ = (5) Volume (4) Å 3 Z 2 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) Crystal size mm 3 Theta range for data collection to Index ranges -11 h 11, -18 k 18, 0 l 24 Reflections collected Independent reflections [R(int) = ] Completeness to theta = % Absorption correction multi-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 10523/0/668 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 S36

37 Table S5: Crystal data and structure refinement parameters for [1-COCH 3 ]BPh 4 Empirical formula C 66 H 59 BNiOP 2 S 2 Formula weight Crystal system monoclinic Space group P 2 1 /c Unit cell dimensions a = (5) Å b = (5) Å c = (9) Å α = 90 β = (3) γ = 90 Volume 6027(3) Å 3 Z 4 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) Crystal size mm 3 Theta range for data collection 5.14 to 50 Index ranges -17 h 18, -17 k 17, -32 l 32 Reflections collected Independent reflections [R(int) = ] Completeness to theta = % Absorption correction multi-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 10517/0/659 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 S37

38 Table S6: Crystal data and structure refinement parameters for [1-CO] 0 Empirical formula C 41 H 36 NiOP 2 S 2 Formula weight Crystal system triclinic Space group P -1 Unit cell dimensions a = (5) Å b = (5) Å c = (5) Å α = (3) β = (3) γ = (3) Volume (12) Å 3 Z 2 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) Crystal size mm 3 Theta range for data collection 3.66 to 50 Index ranges -14 h 14, -14 k 14, -15 l 15 Reflections collected Independent reflections 6179 [R(int) = ] Completeness to theta = % Absorption correction multi-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 6179/0/424 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 S38

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