Supporting Information. Palladium Complexes with Bulky Diphosphine. Synthesis of (Bio-) Adipic Acid from Pentenoic. Acid Mixtures.
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1 Supporting Information Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures. Choon Heng Low, James D. Nobbs,* Martin van Meurs, Ludger P. Stubbs, Eite Drent, Srinivasulu Aitipamula, and Michelle H. L. Pung Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, Singapore, , Leiden University, Leiden Institute of Chemistry, Gorlaeus laboratories, Einsteinweg 55, 2333 CC Leiden S1
2 Table of Contents Single Crystal X-ray Diffraction.... S4 NMR Spectra (Figures S1 S63).... S5 Figure S1. 1 H NMR spectrum of di(tert-butyl)phosphine borane complex... S5 Figure S2. 13 C{ 1 H} NMR spectrum of di(tert-butyl)phosphine borane complex.... S5 Figure S3. 31 P{ 1 H} NMR spectrum of di(tert-butyl)phosphine borane complex.... S6 Figure S4. 1 H NMR spectrum of di(1-adamantanyl)phosphine borane complex.... S6 Figure S5. 13 C{ 1 H} NMR spectrum of di(1-adamantanyl)phosphine borane complex.... S7 Figure S6. 31 P{ 1 H} NMR spectrum of di(1-adamantanyl)phosphine borane complex.... S7 Figure S7. 1 H NMR spectrum of ligand 3... S8 Figure S8. 13 C{ 1 H} NMR spectrum of ligand S8 Figure S9. 31 P{ 1 H} NMR ligand S9 Figure S10. 1 H NMR spectrum of trans-cyclohexane-1,2-diyldimethanol.... S9 Figure S C{ 1 H} NMR spectrum of trans-cyclohexane-1,2-diyldimethanol.... S10 Figure S12. 1 H NMR spectrum of trans-1,2-bis(bromomethyl)cyclohexane.... S10 Figure S13. 1 H NMR spectrum of ligand 4... S11 Figure S C{ 1 H} NMR spectrum of ligand S11 Figure S P{ 1 H} NMR spectrum of ligand S12 Figure S16. 1 H NMR spectrum of ligand 5... S12 Figure S C{ 1 H} NMR spectrum of ligand S13 Figure S P{ 1 H} NMR spectrum of ligand S13 Figure S19. 1 H NMR (400 MHz, CDCl 3 ) spectrum of ligand S14 Figure S C{ 1 H} NMR spectrum of ligand S14 Figure S P{ 1 H} NMR spectrum of ligand S15 Figure S22. 1 H NMR spectrum of ligand 8... S15 Figure S C{ 1 H} NMR spectrum of ligand S16 Figure S P{ 1 H} NMR spectrum of ligand S16 Figure S25. 1 H NMR spectrum of ligand 9... S17 Figure S C{ 1 H} NMR spectrum of ligand S17 Figure S P{ 1 H} NMR spectrum of ligand S18 Figure S28. 1 H NMR spectrum of 9,10,11,15-tetrahydro-9,10-[3,4]furanoanthracene- 12,14-dione.... S18 Figure S C{ 1 H} NMR spectrum of 9,10,11,15-tetrahydro-9,10- [3,4]furanoanthracene-12,14-dione... S19 Figure S30. 1 H NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-cisdimethanol... S19 Figure S C{ 1 H} NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)- cis-dimethanol.... S20 Figure S32. 1 H NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-cisbis(methylene) bis(tosylate).... S20 Figure S C{ 1 H} NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)- cis-bis(methylene) bis(tosylate).... S21 S2
3 Figure S34. 1 H NMR spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)-9,10- dihydro-9,10-ethanoanthracene borane complex.... S21 Figure S P{ 1 H} NMR spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)- 9,10-dihydro-9,10-ethanoanthracene borane complex.... S22 Figure S36. 1 H NMR spectrum of ligand S22 Figure S C{ 1 H} NMR spectrum of ligand S23 Figure S P{ 1 H} NMR spectrum of.ligand S23 Figure S39. 1 H NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-transdicarboxylic acid.... S24 Figure S C{ 1 H} NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-transdicarboxylic acid.... S24 Figure S41. 1 H NMR spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-transdimethanol... S25 Figure S42. 1 H NMR spectrum of trans-11,12-bis(bromomethyl)-9,10-dihydro-9,10- ethanoanthracene... S25 Figure S C{ 1 H} NMR spectrum of trans-11,12-bis(bromomethyl)-9,10-dihydro- 9,10-ethanoanthracene.... S26 Figure S44. 1 H NMR spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)-9,10- dihydro-9,10-ethanoanthracene borane complex.... S26 Figure S P{ 1 H} NMR spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)- 9,10-dihydro-9,10-ethanoanthracene borane complex.... S27 Figure S46. 1 H NMR spectrum of ligand S27 Figure S C{ 1 H} NMR spectrum of ligand S28 Figure S P{ 1 H} NMR spectrum of ligand S28 Figure S49. 1 H NMR spectrum of Pd(4)(O 2 CCF 3 ) 2... S29 Figure S C{ 1 H} NMR spectrum of Pd(4)(O 2 CCF 3 ) S29 Figure S P{ 1 H} NMR spectrum of Pd(4)(O 2 CCF 3 ) S30 Figure S52. 1 H NMR spectrum of Pd(5)(O 2 CCF 3 ) 2... S30 Figure S C{ 1 H} NMR spectrum of Pd(5)(O 2 CCF 3 ) S31 Figure S P{ 1 H} NMR spectrum of Pd(5)(O 2 CCF 3 ) S31 Figure S55. 1 H NMR spectrum of Pd(6)(O 2 CCF 3 ) 2... S32 Figure S C{ 1 H} NMR spectrum of Pd(6)(O 2 CCF 3 ) S32 Figure S P{ 1 H} NMR spectrum of Pd(6)(O 2 CCF 3 ) S33 Figure S58. 1 H NMR spectrum of Pd(10)(O 2 CCF 3 ) 2... S33 Figure S C{ 1 H} NMR spectrum of Pd(10)(O 2 CCF 3 ) S34 Figure S P{ 1 H} NMR spectrum of Pd(10)(O 2 CCF 3 ) S34 Figure S61. 1 H NMR spectrum of Pd(11)(O 2 CCF 3 ) 2... S35 Figure S C{ 1 H} NMR spectrum of Pd(11)(O 2 CCF 3 ) S35 Figure S P{ 1 H} NMR spectrum of Pd(11)(O 2 CCF 3 ) S36 S3
4 Single Crystal X-ray Diffraction. A good quality single crystal grown from the solution crystallization was chosen under a Leica microscope and placed on a fibre needle which was then mounted on to the goniometer of the X-ray diffractometer. X-ray reflections were collected at 110 K on a Rigaku Saturn CCD area detector with graphite monochromated Mo-Kα radiation (λ = Å). Data were collected and processed using CrystalClear (Rigaku) software. Structure was solved by direct methods and SHELX-TL (G. M. Sheldrick, SHELXS-97 and SHELXL Programs for the Solution and Refinement of Crystal Structures, University of Göttingen, Göttingen, Germany) was used for structure solution and least-squares refinement. The non-hydrogen atoms were refined anisotropically. All the H atoms were positioned geometrically and refined using a riding model. CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via /retrieving.html and deposited as Supporting Information. Table S1 Crystallographic data for the molecular complexes described in this paper Compound reference Pd(4)(CF 3 CO 2 ) 2 Pd(5)(CF 3 CO 2 ) 2 Pd(6)(CF 3 CO 2 ) 2 Pd(11)(CF 3 CO 2 ) 2 Chemical formula C 28 H 50 F 6 O 4 P 2 Pd C 24 H 42 F 6 O 4 P 2 Pd C 24 H 46 F 6 O 4 P 2 PdSi C 38 H 52 F 6 O 4 P 2 Pd Formula Mass Crystal system Monoclinic Monoclinic Orthorhombic Monoclinic a/å (2) (6) (3) (2) b/å (3) (4) (2) (2) c/å (2) (3) (3) (2) α/ β/ (3) 94.14(3) (2) γ/ Unit cell volume/å (8) 8857(3) (11) (5) Temperature/K 110(2) 110(2) 110(2) 110(2) Space group P21 C2/c Pna21 P21 No. of formula units per unit cell, Z No. of reflections measured No. of independent reflections R int Final R 1 values (I > 2σ(I)) Final wr(f 2 ) values (I > 2σ(I)) Final R 1 values (all data) Final wr(f 2 ) values (all data) Goodness of fit on F S4
5 NMR Spectra Figure S1. 1 H NMR (400 MHz, CDCl 3 ) spectrum of di(tert-butyl)phosphine borane complex. Figure S2. 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of di(tert-butyl)phosphine borane complex. S5
6 Figure S3. 31 P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of di(tert-butyl)phosphine borane complex. Figure S4. 1 H NMR (400 MHz, CDCl 3 ) spectrum of di(1-adamantanyl)phosphine borane complex. S6
7 Figure S5. 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of di(1-adamantanyl)phosphine borane complex. Figure S6. 31 P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of di(1-adamantanyl)phosphine borane complex. S7
8 Figure S7. 1 H NMR (400 MHz, CDCl 3 ) spectrum of cis-1,2-bis[(di-1-adamantyl)phosphinomethyl)]cyclohexane, 3. Figure S8. 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of cis-1,2-bis[(di-1-adamantyl)phosphinomethyl)]cyclohexane, 3. S8
9 Figure S9. 31 P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of cis-1,2-bis[(di-1-adamantyl)phosphinomethyl)]cyclohexane, 3. Figure S10. 1 H NMR (400 MHz, CDCl 3 ) spectrum of trans-cyclohexane-1,2-diyldimethanol. S9
10 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of trans-cyclohexane-1,2-diyldimethanol. Figure S12. 1 H NMR (400 MHz, CDCl 3 ) spectrum of trans-1,2-bis(bromomethyl)cyclohexane. S10
11 Figure S13. 1 H NMR (400 MHz, CDCl 3 ) spectrum of trans-1,2-bis((di-tert-butylphosphino)methyl)cyclohexane, 4. Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of trans-1,2-bis((di-tert-butylphosphino)methyl)cyclohexane, 4. S11
12 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of trans-1,2-bis((di-tert-butylphosphino)methyl)cyclohexane, 4. Figure S16. 1 H NMR (400 MHz, CDCl 3 ) spectrum of (2-methylenepropane-1,3-diyl)bis(di-tert-butylphosphine), 5. S12
13 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of (2-methylenepropane-1,3-diyl)bis(di-tert-butylphosphine), 5. Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of (2-methylenepropane-1,3-diyl)bis(di-tert-butylphosphine), 5. S13
14 Figure S19. 1 H NMR (400 MHz, CDCl 3 ) spectrum of bis((di-tert-butylphosphino)methyl)dimethylsilane, 6. Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of bis((di-tert-butylphosphino)methyl)dimethylsilane, 6. S14
15 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of bis((di-tert-butylphosphino)methyl)dimethylsilane, 6. Figure S22. 1 H NMR (400 MHz, CDCl 3 ) spectrum of 1,3-bis(di-tert-butylphosphino)propane, 8. S15
16 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of 1,3-bis(di-tert-butylphosphino)propane, 8. Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of 1,3-bis(di-tert-butylphosphino)propane, 8. S16
17 Figure S25. 1 H NMR (400 MHz, CDCl 3 ) spectrum of 1,4-bis(di-tert-butylphosphino)butane, 9. Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of 1,4-bis(di-tert-butylphosphino)butane, 9. S17
18 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of 1,4-bis(di-tert-butylphosphino)butane, 9. Figure S28. 1 H NMR (400 MHz, CDCl 3 ) spectrum of 9,10,11,15-tetrahydro-9,10-[3,4]furanoanthracene-12,14-dione. S18
19 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of 9,10,11,15-tetrahydro-9,10-[3,4]furanoanthracene-12,14-dione. Figure S30. 1 H NMR (400 MHz, d 6 -DMSO) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-cis-dimethanol. S19
20 Figure S C{ 1 H} NMR (101 MHz, d 6 -DMSO) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-cis-dimethanol. Figure S32. 1 H NMR (400 MHz, CDCl 3 ) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-cis-bis(methylene) bis(tosylate). S20
21 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-cis-bis(methylene) bis(tosylate). Figure S34. 1 H NMR (400 MHz, CDCl 3 ) spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene borane complex. S21
22 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene borane complex. Figure S36. 1 H NMR (400 MHz, CDCl 3 ) spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene, 10. S22
23 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene, 10. Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of cis-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene, 10. S23
24 Figure S39. 1 H NMR (400 MHz, d 6 -DMSO) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid. Figure S C{ 1 H} NMR (101 MHz, d 6 -DMSO) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid. S24
25 Figure S41. 1 H NMR (400 MHz, CDCl 3 ) spectrum of 9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)-trans-dimethanol. Figure S42. 1 H NMR (400 MHz, CDCl 3 ) spectrum of trans-11,12-bis(bromomethyl)-9,10-dihydro-9,10-ethanoanthracene. S25
26 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of trans-11,12-bis(bromomethyl)-9,10-dihydro-9,10-ethanoanthracene. Figure S44. 1 H NMR (400 MHz, CDCl 3 ) spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene borane complex. S26
27 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene borane complex. Figure S46. 1 H NMR (400 MHz, CDCl 3 ) spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene, 11. S27
28 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene, 11. Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of trans-11,12-bis((di-tert-butylphosphino)methyl)-9,10-dihydro-9,10- ethanoanthracene, 11. S28
29 Figure S49. 1 H NMR (400 MHz, CDCl 3 ) spectrum of Pd(4)(O 2 CCF 3 ) 2. Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of Pd(4)(O 2 CCF 3 ) 2. S29
30 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of Pd(4)(O 2 CCF 3 ) 2. Figure S52. 1 H NMR (400 MHz, CDCl 3 ) spectrum of Pd(5)(O 2 CCF 3 ) 2. S30
31 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of Pd(5)(O 2 CCF 3 ) 2. Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of Pd(5)(O 2 CCF 3 ) 2. S31
32 Figure S55. 1 H NMR (400 MHz, CDCl 3 ) spectrum of Pd(6)(O 2 CCF 3 ) 2. Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of Pd(6)(O 2 CCF 3 ) 2. S32
33 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of Pd(6)(O 2 CCF 3 ) 2. Figure S58. 1 H NMR (400 MHz, CDCl 3 ) spectrum of Pd(10)(O 2 CCF 3 ) 2. S33
34 Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of Pd(10)(O 2 CCF 3 ) 2. Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of Pd(10)(O 2 CCF 3 ) 2. S34
35 Figure S61. 1 H NMR (400 MHz, CDCl 3 ) spectrum of Pd(11)(O 2 CCF 3 ) 2. Figure S C{ 1 H} NMR (101 MHz, CDCl 3 ) spectrum of Pd(11)(O 2 CCF 3 ) 2. S35
36 Figure S P{ 1 H} NMR (162 MHz, CDCl 3 ) spectrum of Pd(11)(O 2 CCF 3 ) 2. S36
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