Iron Complexes of a Bidentate Picolyl NHC Ligand: Synthesis, Structure and Reactivity
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supplementary Information for Iron Complexes of a Bidentate Picolyl HC Ligand: Synthesis, Structure and Reactivity Qiuming Liang, Trevor Janes, Xhoana Gjergji and Datong Song* Davenport Chemical Research Laboratories, Department of Chemistry, University of Toronto 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6 dsong@chem.utoronto.ca; Tel: ; Fax: X-ray crystallography S2 2. MR spectra S4 3. IR spectra S9 4. C-C coupling reaction S11 5. References S14 S1
2 1. X-ray Crystallography The X-ray diffraction data were collected on a uker Kappa Apex II diffractometer with graphite-monochromated Mo Kα radiation (λ = Å) at 150 K controlled by an Oxford Cryostream 700 series low-temperature system and processed with the uker Apex 2 software package. 1 The structures were solved by direct methods and refined using SHELX-2013 and SHELX-2014 software packages. 2,3 All non-hydrogen atoms were refined anisotropically, except for those involved in the disordered THF molecules in the lattice of 1. All hydrogen atoms were calculated using the riding model. The disordered THF molecules in the lattice of 1 were successfully modeled using two sets of coordinates with the occupancies constrained to a 1:1 ratio. The diffuse residual electron density from solvent molecules in the lattice of 4 was removed with the SQUEEZE function of PLATO 4 and was not included in the formula or the refinement. Selected crystallographic data are summarized in Tables S1 S2. Table S1. Selected crystallographic data for compounds (2THF) Empirical formula C 44 H 54 6 O 2 2 C 24 H 37 4 Si 2 C 18 H C 36 H 36 6 FW (g mol -1 ) Crystal system Monoclinic Triclinic Monoclinic Monoclinic Space Group P 2 1 /n P -1 P 2 1 /n I 2/a Z a (Å) (1) (9) (7) (2) b (Å) (8) (1) (6) (6) c (Å) (2) (2) (9) (3) (deg) (4) (deg) (3) (6) (3) (6) (deg) (4) V (Å 3 ) (5) (4) (2) 6701(1) D calcd, (g cm -3 ) (mm -1 ) F(000) no. of obsd reflns no. of params refnd goodness of fit R 1 (I>2σ) wr 2 (I>2σ) S2
3 Table S2. Selected crystallographic data for compounds Empirical formula C 25 H 26 3 C 32 H 33 3 C 21 H 19 3 O 3 C 22 H 19 3 O 4 FW (g mol -1 ) Crystal system Triclinic Triclinic Monoclinic Monoclinic Space Group P-1 P-1 P2 1 /n P2 1 /c Z a (Å) 8.041(2) (9) (2) (1) b (Å) (2) 9.846(1) 8.828(1) (1) c (Å) (3) (1) (2) (9) (deg) (7) (4) (deg) (8) (4) (6) (4) (deg) (8) (4) V (Å 3 ) (4) (2) (5) (3) D calcd, (g cm -3 ) (mm -1 ) F(000) no. of obsd reflns no. of params refnd goodness of fit R 1 (I>2σ) wr 2 (I>2σ) S3
4 2. MR spectra HMDS Figure S1. 1 H MR (600 MHz, C 6 D 6 ) spectrum of [(HL)(HMDS)] (2). Figure S2. 1 H MR (600 MHz, CDCl 3 ) spectrum of [ 2 (HL)] (3). S4
5 Figure S3. 1 H MR (600 MHz, C 6 D 6 ) spectrum of L 2 (4). CH 2 Ph Figure S4. 1 H MR (600 MHz, C 6 D 6 ) spectrum of [Bn(HL)] (5). ote: the poor quality of the spectrum is due to low solubility. S5
6 CH 2 Ph CH 2 Ph Figure S5. 1 H MR (600 MHz, C 6 D 6 ) spectrum of [(Bn) 2 (HL)] (6). Figure S6. 1 H MR (600 MHz, CD 2 Cl 2 ) spectrum of [() 3 (HL)] (7). S6
7 Figure S7. 13 C MR (151 MHz, CD 2 Cl 2 ) spectrum of [() 3 (HL)] (7). O Figure S8. 1 H MR (600 MHz, CDCl 3 ) spectrum of dibenzyl ketone. S7
8 O Figure S9. 13 C MR (151 MHz, CDCl 3 ) spectrum of dibenzyl ketone. Figure S10. 1 H MR (600 MHz, CD 2 Cl 2 ) spectrum of [() 4 (HL)] (8). S8
9 Figure S C MR (151 MHz, CD 2 Cl 2 ) spectrum of [() 4 (HL)] (8). 3. IR spectra Transmittance [%] Wavenumber cm Figure S12. IR spectrum of [() 3 (HL)] (7) as a neat solid. S9
10 Transmittance [%] Wavenumber cm Transmittance [%] Wavenumber cm Figure S13. IR spectra of [() 4 (HL)] (8): neat solid sample (top) and solution (bottom). C:\Users\Walter\Desktop\HL4-THF.0 Sample description Instrument type and / or accessory 2016/8/2 Page 1/1 S10
11 4. C-C coupling reaction Scheme S1. C C bond formation reaction. CH 2 Ph CH 2 Ph + 1eq. Et 2 O, R.T., 1 hr 6 OMe I (35%) II (49%) III (28%) Figure S14. GC trace of the CC bond formation reaction mixture run 1. Retention times: C 6 Me min, I min, II min, III min. 1.6 mg of C 6 Me 6 was used as internal standard. Figure S14. GC trace of the CC bond formation reaction mixture run 2. Retention times: C 6 Me min, I min, II min, III min. 2.6 mg of C 6 Me 6 was used as internal standard. S11
12 Yield Calculations for run 1: Compound 6 (17.7mg, 34.4 µmol), p-methoxybenzyl bromide (5 µl, 34.3 µmol), C 6 Me 6 (1.6 mg, 9.9 µmol) CH 2 Ph CH 2 Ph 6 I n( I) 9.9 mol 12.5 mol 12.5 mol %yield 36% mol II n( II) 9.9 mol 17.0 mol 17.0 mol %yield 49% mol OMe 0.5 III n( III) 9.9 mol 4.5 mol 4.5 mol 2 %yield 26% mol Conversion of p-methoxybenzyl bromide: 49% + 26% = 75% S12
13 Yield Calculations for run 2: Compound 6 (17.7mg, 34.4 µmol), p-methoxybenzyl bromide (5 µl, 34.3 µmol), C 6 Me 6 (2.6 mg, 16.0 µmol) CH 2 Ph CH 2 Ph 6 I n( I) 16.0 mol 11.4 mol 11.4 mol %yield 33% mol II n( II) 16.0 mol 17.0 mol 17.0 mol %yield 49% mol OMe 0.5 III n( III) 16.0 mol 5.0 mol 5.0 mol 2 %yield 29% mol Conversion of p-methoxybenzyl bromide: 49% + 29% = 78% Average yield of I = (36%+33%)/2 = 35% Average yield of II = (49%+49%)/2 = 49% Average yield of III = (26%+29%)/2 = 28% Average conversion of p-methoxybenzyl bromide = (75%+78%)/2 = 77% S13
14 5. References: 1. Apex 2 Software Package; uker AXS Inc., Madison, WI, Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, (accessed on July 4, 2013 and September 4, 2015). 4. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7. S14
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