chapter 2 palladium catalysts in suzuki cross- coupling reaction

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pA 800 600 400 200 FID1 A, (ORTAK\ORTAK094\G180SUZ1.D) 4-bromoanisole 0 0 2 4 6 8 10 12 14 16 18 9.529 hexadecane 14.516 15.325 4-methoxybiphenyl Figure 4.3. GC chromatogram of a selected Suzuki Reaction (4-bromoanisole and phenylboronic acid) 4.3.1.1. Calculation of Reactant and Product Amount on GC For the calculation of amount of reactants and products, response factor of each reactant and product for the set temperature program of GC was determined. As internal standard, hexadecane was used. The amount of internal standard does not change throughout the reaction, so the response factor of each compound was determined according to the amounts and areas under the peaks of internal standard and standard compound of interest. For the determination of response factor of a compound, a known amount of standard compound together with a known amount of internal standard dissolved in the reaction solvent and diluted with ethyl acetate, and then was injected to GC. After the analysis is complete according to the set temperature program, the following equation is used for the determination of response factor of that compound: R.F. = internal standart area compound area compound amount x (4.2) internal standart amount In Suzuki experiments response factor values for the reactant and products were determined with respect to hexadecane as internal standard. In order to calculate the min 46
amount of both reactant and products at the end of reaction, aliquots of reaction sample taken from the reaction flask and diluted samples were injected to GC. At the end of GC analysis, taking the amount of hexadecane and the area under the hexadecane peak into account, the following equation was used in order to calculate the amount of reactant and products at the end of reaction: amount of compound = internal standart amount internal standart area x R.F. x compound area (4.3) 4.3.1.2. Calculation of Reactant Conversion, Product Yield and Recovery Reactant conversion at any time is calculated using equation 4.4: (Reactant Conversion) t % = (Reactant) i - (Reactant) t (Reactant) i x 100 (4.4) where (reactant)i is the weight of reactant at the beginning of the reaction and (reactant)t is the weight of reactant at time t. 4.5: Product yield of a molecule was calculated according to the following equation Product Yield = mole of product t initial mole of aryl halide (4.5) 47
Page 1 and 2:
SHORT-TIME SUZUKI REACTIONS OF ARYL
Page 3 and 4:
ACKNOWLEDGEMENTS Firstly, I’d lik
Page 5 and 6:
ÖZET ARİL HALOJENÜRLERİN HAVA A
Page 7 and 8: 3.2.2. Catalysts Anchored to Inorga
Page 9 and 10: LIST OF FIGURES Figure Page Figure
Page 11 and 12: Figure A.27. 13 C NMR of 4-cyanobip
Page 13 and 14: CHAPTER 1 INTRODUCTION The palladiu
Page 15 and 16: CHAPTER 2 PALLADIUM CATALYSTS IN SU
Page 17 and 18: 2.1.2. The Coordination Geometry of
Page 19 and 20: R 1 R 1 4. Sonogashira Reaction: H
Page 21 and 22: 2.2.1. Mechanism of Suzuki Coupling
Page 23 and 24: As a result, organic group or hydri
Page 25 and 26: 2.2.2.2. Halogen Effect Nearly all
Page 27 and 28: found to be excellent complexes for
Page 29 and 30: R Table 2.2. Examples from literatu
Page 31 and 32: L R Pd X R Pd L OR'' X L L + OR' R'
Page 33 and 34: omides and iodides is performed eff
Page 35 and 36: times for the transformation of a l
Page 37 and 38: R Br + (HO) 2B R' 5% Pd(OAc) 2 15%
Page 39 and 40: of insoluble solids are among the m
Page 41 and 42: could be reused multiple times. The
Page 43 and 44: 3.2.2. Catalysts Anchored to Inorga
Page 45 and 46: SO 2NH N Pd SO 2 N SO 2 NH NH H O1.
Page 47 and 48: utilized them in Heck and Suzuki co
Page 49 and 50: Smith et al introduced the use of P
Page 51 and 52: • Complexes immobilized in zeolit
Page 53 and 54: 3.3.3. Preparation of Zeolite-Suppo
Page 55 and 56: CHAPTER 4 EXPERIMENTAL STUDY 4.1. P
Page 57: temperature, the catalyst was recov
Page 61 and 62: 4-Methoxybiphenyl: 1 H NMR (400 MHz
Page 63 and 64: 51 Table 4.1. Purification of coupl
Page 65 and 66: CHAPTER 5 RESULTS AND DISCUSSIONS I
Page 67 and 68: Table 5.2. The effect of base on Pd
Page 69 and 70: Table 5.4. The Optimization of Pd-N
Page 71 and 72: H 3COC Table 5.5. Effect of zeolite
Page 73 and 74: Table 5.6. Pd(NH3)4 2+ -loaded NaY
Page 75 and 76: The type of other organic co-solven
Page 77 and 78: yield was very low (Table 5.8, entr
Page 79 and 80: evealed excellent reactivity toward
Page 81 and 82: CHAPTER 6 CONCLUSIONS In this thesi
Page 83 and 84: REFERENCES Albisson, D.A., Bedford,
Page 85 and 86: Choudary, B.M., Madhi, S., Chowdari
Page 87 and 88: Heiden, M. Plenio, H. 2004. ‘‘H
Page 89 and 90: Coupling Reactions of Aryl Chloride
Page 91 and 92: Phan, N.T.S., Brown, D.H., Styring,
Page 93 and 94: Wolfe, J.P., Singer, R.A., Yang, B.
Page 95 and 96: Figure A.1. 13 C NMR of 1-phenylnap
Page 97 and 98: Figure A.3. 13 C NMR of 2-acetylbip
Page 99 and 100: Figure A.5 . 13 C NMR of 2-methoxyb
Page 101 and 102: Figure A.7. 13 C NMR of 2-methylbip
Page 103 and 104: Figure A.9. 13 C NMR of 2-phenylnap
Page 105 and 106: Figure A.11. 13 C NMR of 3-acetylbi
Page 107 and 108: Figure A.13. 13 C NMR of 3-methoxyb
Page 109 and 110:
Figure A.15. 13 C NMR of 3-phenylpy
Page 111 and 112:
Figure A.17. 13 C NMR of 4-acetyl-4
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Figure A.19. 13 C NMR of 4-methoxyb
Page 115 and 116:
Figure A.21. 13 C NMR of 4-methylbi
Page 117 and 118:
Figure A.23. 13 C NMR of 4-phenylbe
Page 119 and 120:
Figure A.25. 13 C NMR of 4-acetylbi
Page 121 and 122:
Figure A.27. 13 C NMR of 4-cyanobip
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Figure A.29. 13 C NMR of 4-nitrobip
Page 125 and 126:
Figure A.31. 13 C NMR of 4-phenylan
Page 127 and 128:
APPENDIX B MASS SPECTRUMS OF SUZUKI
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Figure B.2. Mass spectrum of 2-acet
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Figure B.4. Mass spectrum of 2-meth
Page 133 and 134:
Figure B.6. Mass spectrum of 3-acet
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Figure B.8. Mass spectrum of 3-phen
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Figure B.10. Mass spectrum of 4-phe
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Figure B.12. Mass spectrum of 4-met
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Figure B.14. Mass spectrum of 4-cya
Page 143:
Figure B.16. Mass spectrum of 4-met
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