Supplementary Information for: E-H Bond Activations and Hydrosilylation Catalysis with Iron and Cobalt Metalloboranes
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1 Supplementary Information for: E-H Bond Activations and Hydrosilylation Catalysis with Iron and Cobalt Metalloboranes Mark A. Nesbit, Daniel L. M. Suess, Jonas C. Peters* Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, California 91125, United States Contents Table S1. XRD experimental parameters for 1a, 1b, 1c, 1d. Table S2. XRD experimental parameters for 2, 2a, 2b, 2c, 2-Br. Figure S1. ORTEP representation of the asymmetric unit for 2. Figure S2. ORTEP representation of 2-Br. Figure S3. 1 H NMR spectra of a mixture of isomers of 1d at C, 25 0 C, 75 0 C Figure S4. 77 K X-Band EPR spectrum of 2c in 2-MeTHF. Figure S5. 77 K X-Band EPR spectrum of 2d in toluene. Figure S6. Thin Film IR spectrum of 2d. Figure S7. 1 H NMR spectrum of 1b. Figure S8. 1 H NMR spectrum of 1d. Figure S9. 1 H NMR spectrum of 2. Figure S10. 1 H NMR spectrum of 2a. Page S2 S3 S4 S5 S5 S6 S6 S7 S7 S8 S8 S9 Figure S11-S18. Representative 1 H NMR spectra of catalytic runs. S9-13 S1
2 Table S1. XRD experimental parameters for 1a, 1b, 1c, 1d Compound 1a 1b 1c 1d Chemical Formula C 36 H 46 BP 2 OFe C 72 H 94 B 2 P 4 S 2 Fe C 43 H 50 BNP 2 Fe C 39 H 49 BN 2 P 2 Fe Formula Weight T (K) 100(2)K 100(2)K 100(2)K 100(2)K λ (Å) Space Group C 2 /c P2 1 /n P2 1 /n P2 1 /n A (7) (9) (5) (10) B (4) (15) (6) (15) C (14) (13) (13) (11) Α Β (11) (5) (2) (5) Γ Volume (5) (5) (3) (5) Z Density (calc) R1, wr , , , , R1 = F o - F c / F o, wr2 = { [w(f o 2 - F c 2 ) 2 ]/ w(f o 2 ) 2 } 1/2 S2
3 Table S2. XRD experimental parameters for 2, 2a, 2b, 2c, 2-Br Compound 2 2a 2b 2c 2-Br C 30 H 463 BN 2 P 2 Co C 36 H 46 BP 2 OCo C 36 H 46 BP 2 SCo C 43 H 50 BNP 2 Co C 30 H 41 BP 2 BrCo Formula Weight T (K) 100(2)K 100(2)K 100(2)K 100(2)K 100(2)K λ (Å) Space Group P-1 P2 1 /c P2 1 /n Pca2 1 C2/c A (7) (14) (4) (2) (11) B (12) (6) (7) (13) (6) C (15) (15) (6) (12) (19) Α (5) Β (4) (4) (16) (3) Γ (3) Volume (5) (4) (2) (6) (6) Z Density (calc) R1, wr , , , , , R1 = F o - F c / F o, wr2 = { [w(f o 2 - F c 2 ) 2 ]/ w(f o 2 ) 2 } 1/2 S3
4 Figure S1. ORTEP representation of the asymmetric unit for 2 (H atoms omitted for clarity). Color Scheme: blue = nitrogen, purple = phosphorus, gold = boron, green = cobalt, black = carbon. S4
5 Figure S2. ORTEP Representation of 2-Br (H atoms omitted for clarity). Selected Bond distances Co1-P (2) Å; Co1-P (2) Å; Co1-C (6) Å; Co1-C (7) Å; Co1-B (7) Å; Co1-Br (16) Å. Figure S3. Variable temperature 1 H NMR of the reaction mixture of 1d in d 8 -toluene. Red trace is at C, green trace is at 25 0 C, blue trace is at 75 0 C. *Et 2 O. % THF. S5
6 B (Gauss) Figure S4. 77 K X-Band EPR spectrum of 2c in 2-MeTHF (top trace, blue) and simulation (bottom trace, green). Simulation Parameters: g 1 : 2.017, g 2 : 2.199, g 3 : HStrain 1 : MHz, HStrain 2 : MHz, HStrain 3 : MHz. A P1 = 63 MHz, 1 MHz, 62.7 MHz; A P2 : 63 MHz, 1 MHz, 30.1 MHz; A H : 30.0 MHz, 1 MHz, 1 MHz; A N : 30.0 MHz, MHz, MHz; A Co : MHz, 19.7 MHz, 1.0 MHz. Microwave Frequency: GHz, Range: 2770 G G. Figure S5. 77 K X-band EPR spectrum of 2d (top trace, blue) and simulation (bottom trace, green). Simulation Parameters: g 1 : , g 2 : , g 3 : HStrain 1 : MHz, HStrain 2 : MHz, HStrain 3 : MHz. A Co : MHz, MHz, MHz. Microwave Frequency: GHz, Range: 2800 G G. S6
7 Absorbance ν (cm - 1 ) Figure S6. Thin film IR spectrum of 2d from evaporated C 6 D 6. Figure S7. 1 H NMR spectrum of 1b in C 6 D 6. *Et 2 O. % residual silicone grease. S7
8 Figure S8. 1 H NMR spectrum of 1d in d 8 -toluene (mixture of isomers). *d 8 -toluene. S8
9 Figure S9. 1 H NMR spectrum of 2 in C 6 D 6. Figure S10. 1 H NMR spectrum of 2a in C 6 D 6. S9
10 Figure S11. 1 H NMR spectrum of the reaction mixture of Ph 2 SiH 2 with propanal in 5:1 THF:d 8 -THF catalyzed by 2. *Ferrocene internal standard. Figure S12. 1 H NMR spectrum of the reaction mixture of Ph 2 SiH 2 with butanal in 4:1 THF:d 8 -THF catalyzed by 2. Figure S13. 1 H NMR spectrum of the reaction mixture of Ph 2 SiH 2 with pentanal in 4:1 THF:d 8 -THF catalyzed by 2. *Ferrocene internal standard S10
11 Figure S14. 1 H NMR spectrum of the reaction mixture of Ph 2 SiH 2 with cyclohexanone in 5:1 THF:d 8 -THF catalyzed by 2. *Ferrocene internal standard. & Ph 2 SiH 2. # cyclohexanone. Figure S15. 1 H NMR spectrum of the reaction mixture of 2-pentanone with Ph 2 SiH 2 in C 6 D 6 catalyzed by 2. *Ferrocene internal standard. S11
12 Figure S16. 1 H NMR spectrum of the reaction mixture of acetophenone with Ph 2 SiH 2 in C 6 D 6 catalyzed by 2. *Ferrocene internal standard. S12
13 Figure S17. 1 H NMR spectrum of the reaction mixture of benzophenone and Ph 2 SiH 2 in C 6 D 6 catalyzed by 2. *Ferrocene internal standard. & Ph 2 SiH 2. Figure S18. 1 H NMR spectrum of the reaction mixture of benzaldehyde and Ph 2 SiH 2 in C 6 D 6 catalyzed by 2. * Ferrocene internal standard. & Ph 2 SiH 2. # benzaldehyde. S13
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