chapter 2 palladium catalysts in suzuki cross- coupling reaction

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Figure 3.17. Molecular modeling of the Pd complexes ([Pd(NH3)4] 2+ , [Pd(OAc)2], [Pd(C3H5)Cl]2 in Na-Y zeolite using the CAChe TM software with extended MM2 molecular force field and molecular mechanics methods..................................................................... H42 Figure 4.1. Preparation of [Pd(NH3)4] +2 -Y catalyst from NaY zeolite............................. H43 Figure 4.2. The experimental set-up for Suzuki coupling reactions................................. H45 Figure.4.3. GC chromatogram of a selected Suzuki Reaction (4-bromoanisole and phenylboronic acid) ...................................................... H46 Figure A.1. 13 C NMR of 1-phenylnaphthalene...................................................................83 Figure A.2. 1 H NMR of 1-phenylnaphthalene…………………………………………....84 Figure A.3. 13 C NMR of 2-acetylbiphenyl ........................................................................85 Figure A.4. 1 H NMR of 2-acetylbiphenyl..........................................................................86 Figure A.5. 13 C NMR of 2-methoxybiphenyl....................................................................87 Figure A.6. 1 H NMR of 2-methoxybiphenyl .....................................................................88 Figure A.7. 13 C NMR of 2-methylbiphenyl.......................................................................89 Figure A.8. 1 H NMR of 2-methylbiphenyl........................................................................90 Figure A.9. 13 C NMR of 2-phenylnaphthalene..................................................................91 Figure A.10. 1 H NMR of 2-phenylnaphthalene.................................................................92 Figure A.11. 13 C NMR of 3-acetylbiphenyl ......................................................................93 Figure A.12. 1 H NMR of 3-acetylbiphenyl........................................................................94 Figure A.13. 13 C NMR of 3-methoxybiphenyl..................................................................95 Figure A.14. 1 H NMR of 3-methoxybiphenyl ...................................................................96 Figure A.15. 13 C NMR of 3-phenylpyridine......................................................................97 Figure A.16. 1 H NMR of 3-phenylpyridine.......................................................................98 Figure A.17. 13 C NMR of 4-acetyl-4’-methoxybiphenyl ..................................................99 Figure A.18. 1 H NMR of 4-acetyl-4’-methoxybiphenyl..................................................100 Figure A.19. 13 C NMR of 4-methoxybiphenyl................................................................101 Figure A.20. 1 H NMR of 4-methoxybiphenyl .................................................................102 Figure A.21. 13 C NMR of 4-methylbiphenyl...................................................................103 Figure A.22. 1 H NMR of 4-methylbiphenyl....................................................................104 Figure A.23. 13 C NMR of 4-phenylbenzaldehyde ...........................................................105 Figure A.24. 1 H NMR of 4-phenylbenzaldehyde ............................................................106 Figure A.25. 13 C NMR of 4-acetylbiphenyl ....................................................................107 Figure A.26. 1 H NMR of 4-acetylbiphenyl......................................................................108 x
Figure A.27. 13 C NMR of 4-cyanobiphenyl ....................................................................109 Figure A.28. 1 H NMR of 4-cyanobiphenyl......................................................................110 Figure A.29. 13 C NMR of 4-nitrobiphenyl ......................................................................111 Figure A.30. 1 H NMR of 4-nitrobiphenyl........................................................................112 Figure A.31. 13 C NMR of 4-phenylaniline.......................................................................113 Figure A.32. 1 H NMR of 4-phenylaniline........................................................................114 Figure B.1. Mass spectrum of 1-phenylnaphthalene……………………………............116 Figure B.2. Mass spectrum of 2-acetylbiphenyl..............................................................117 Figure B.3. Mass spectrum of 2-methoxybiphenyl..........................................................118 Figure B.4. Mass spectrum of 2-methylbiphenyl ............................................................119 Figure B.5. Mass spectrum of 2-phenylnaphthalene .......................................................120 Figure B.6. Mass spectrum of 3-acetylbiphenyl..............................................................121 Figure B.7. Mass spectrum of 3-methoxybiphenyl..........................................................122 Figure B.8. Mass spectrum of 3-phenylpyridine .............................................................123 Figure B.9. Mass spectrum of 4-acetylbiphenyl..............................................................124 Figure B.10. Mass spectrum of 4-phenylbenzaldehyde...................................................125 Figure B.11. Mass spectrum of 4-acetyl-4’-methoxybiphenyl........................................126 Figure B.12. Mass spectrum of 4-methoxybiphenyl.........................................................127 Figure B.13. Mass spectrum of 4-nitrobiphenyl……………......................…...……..…128 Figure B.14. Mass spectrum of 4-cyanobiphenyl.............................................................129 Figure B.15. Mass spectrum of 4-phenylaniline...............................................................130 Figure B.16. Mass spectrum of 4-methylbiphenyl............................................................131 xi
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: LIST OF FIGURES Figure Page Figure
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 and 58: temperature, the catalyst was recov
Page 59 and 60: amount of both reactant and product
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
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The type of other organic co-solven
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yield was very low (Table 5.8, entr
Page 79 and 80:
evealed excellent reactivity toward
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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
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Figure A.31. 13 C NMR of 4-phenylan
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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
Page 137 and 138:
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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